Benzoyl isothiocyanate → HCID 2809010, compound

HRID 1191082Notes

Reaction equation

HRID 1191082 reaction equation
[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:12]1([CH2:15][NH2:16])[CH2:14][CH2:13]1>C(Cl)(Cl)Cl>[C:1]([NH:9][C:10]([NH:16][CH2:15][CH:12]1[CH2:14][CH2:13]1)=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 75646Cyclopropanemethanamine

Product 1

HCID 2809010HCID 2809010, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Add benzoyl isothiocyanate (500 g, 3.06 mol) to chloroform (5 L) and cool to <5° C. Add a solution of cyclopropylmethylamine (230 g, 3.22 mol) in chloroform (500 mL) with vigorous stirring maintaining a temperature below 20° C. Remove the ice-water bath, and stir the mixture at room temperature overnight. Concentrate the mixture in vacuo to obtain the desired intermediate as a white solid (720 g, 100%). MS (APCI) m/z: 235 (M+H)+.

Workup

  1. temperaturecool to <5° C
  2. temperaturemaintaining a temperature below 20° C
  3. customRemove the ice-water bath
  4. stirringstir the mixture at room temperature overnight
  5. concentrationConcentrate the mixture in vacuo

Sources & evidence

ORD record
ord-e1892da54db2480aa07a4ac34842f6c2
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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