N,N′-Bis-tert-butoxycarbonylthiourea Chemical Properties

Melting point:

131-135 °C(lit.)

Density 

1.152

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

5.55±0.70(Predicted)

form 

powder to crystal

color 

White to Almost white

InChI

InChI=1S/C11H20N2O4S/c1-10(2,3)16-8(14)12-7(18)13-9(15)17-11(4,5)6/h1-6H3,(H2,12,13,14,15,18)

InChIKey

CSOJECDGWHHWRS-UHFFFAOYSA-N

SMILES

C(C)(C)(C)OC(=O)NC(=S)NC(=O)OC(C)(C)C

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29302000

MSDS

• Language:English Provider:SigmaAldrich

N,N′-Bis-tert-butoxycarbonylthiourea Usage And Synthesis

Chemical Properties

White to off-white solid

Uses

N,N′-Di-Boc-thiourea (N,N′-di-Boc-substituted thiourea), also known as di-Boc-thiourea is a thioacylating agent for preparing thiocarbonyl compounds.
N,N′-Di-Boc-thiourea (di-Boc protected thiourea) may be used as a guanylating agent for the synthesis of guanidines, via guanylation of amines in the presence of Mukaiyama′s reagent as a promoter.

Uses

N,N''-Di(tert-butoxycarbonyl)thiourea is used in the preparation of bis-imidazoline diphenyl derivatives as α1-adrenoceptor antagonists.

Synthesis

GENERAL METHOD: To an anhydrous tetrahydrofuran (120 mL) solution of thiourea (500 mg, 6.58 mmol) was slowly added a suspension of 60% sodium hydride in mineral oil (1184 mg, 29.61 mmol) at 0 °C under argon protection. The reaction mixture was stirred at room temperature for 30 min to ensure complete formation of the anion and subsequently cooled to 0°C. At this temperature, di-tert-butyl dicarbonate (3155 mg, 14.47 mmol) was added dropwise. The reaction mixture was stirred at room temperature overnight and then cooled to 0 °C again. Water (20 mL) was added slowly and dropwise to quench the reaction. The aqueous phase was extracted with ethyl acetate (3 x 50 mL). The combined organic phases were washed sequentially with brine (30 mL) and water (30 mL) and dried with anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, purification by cold hexane grinding gave N,N'-di-Boc-thiourea as a white crystalline solid (1019 mg, 90% yield). The product has a melting point of 120-122°C and a clear melting range.1H NMR (400 MHz, CDCl3) data: δ 1.57 (s, 18H, CH3, Boc), 3.93 (br s, 2H, NH).

References

[1] Chemistry - A European Journal, 2016, vol. 22, # 9, p. 3009 - 3018
[2] Tetrahedron Letters, 1992, vol. 33, # 40, p. 5933 - 5936
[3] Tetrahedron Letters, 2013, vol. 54, # 30, p. 3982 - 3984
[4] Patent: US2018/127358, 2018, A1. Location in patent: Paragraph 0202; 0203
[5] Journal of Organic Chemistry, 2001, vol. 66, # 12, p. 4206 - 4213

N,N′-Bis-tert-butoxycarbonylthiourea(145013-05-4)Related Product Information

• METHYLENE DIURETHANE
• N-BOC THIOUREA 97
• DIMETHYLOLTHIOUREA
• N,N′-Bis-tert-butoxycarbonylthiourea