Tert-Butylamine → N-(tert-butylcarbamothioyl)benzamide

HRID 1395098Notes

Reaction equation

HRID 1395098 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[C:6]([N:14]=[C:15]=[S:16])(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC(C)=O>[C:6]([N:14]=[C:15]=[N:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:6]([NH:14][C:15]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[S:16])(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 6385Tert-Butylamine2×HCID 11776TriphenylphosphineHCID 68284Benzoyl isothiocyanate2×HCID 5462977Diethyl azodicarboxylate

Product 2

HCID 909198N-(tert-butylcarbamothioyl)benzamideYield 52%HCID 20340157HCID 20340157, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-Benzoyl-N'-(t-butyl)carbodiimide was prepared by the method of O. Misunobu et al (Bull. Chem. Soc. Japan, 45, p. 3607, 1972) in two steps from t-butylamine, benzoyl isothiocyanate, diethylazodicarboxylate and triphenylphosphine. The initial reaction combined equimolar amounts (0.04 m) of benzoyl isothiocyanate and t-butylamine in 125 ml of dry acetone. After two hours at ambient temperature and 0.5 hour at 40° C., the solution was evaporated to dryness and the precipitate washed with petroleum ether and recrystallized from acetonitrile to yield N-benzoyl-N'-(t-butyl)thiourea (52%), mp 128.5°-130° C. To this was added an equivalent of diethylazodicarboxylate in 100 ml of tetrahydrofuran, and the solution was allowed to stir three days. After the addition of triphenylphosphine the solution stirred an additional ten days, the solvent was evaporated and the residue was extracted with petroleum ether, dried over sodium sulfate and then distilled to yield 38% of N-benzoyl-N'-(t-butyl)carbodiimide, bp 94 (0.04 torr), lit. bp 110° C. (0.55 m).

Workup

  1. customThe initial reaction
  2. custom0.5 hour at 40° C., the solution was evaporated to dryness
  3. washthe precipitate washed with petroleum ether
  4. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-869b0ff876a041c98dbd376ea32f6662
Source dataset
uspto-grants-1980_05
Patent number
US04202786

Reaction notes

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