Benzoyl isothiocyanate → t-Butyl 3-amino-2-(N-benzoylthiocarbamoyl)crotonate

HRID 851538Notes

Reaction equation

HRID 851538 reaction equation
[NH2:1]/[C:2](/[CH3:11])=[CH:3]\[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[C:12]([N:20]=[C:21]=[S:22])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(OCC)C>[NH2:1]/[C:2](/[CH3:11])=[C:3](/[C:21](=[S:22])[NH:20][C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)\[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 12221517tert-Butyl 3-aminocrotonate

Product 1

HCID 86738557t-Butyl 3-amino-2-(N-benzoylthiocarbamoyl)crotonateYield 43.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of t-butyl 3-aminocrotonate (65.3 g, 0.4 mol), benzoyl isothiocyanate (62.9 g, 0.4 mol), and diethyl ether (300 ml) was stirred at ambient temperature for 3 hours. The solid product was collected on a filter, washed with ether and dried to give 56 g (43.7 percent yield) of material melting at 107° to 110° C.

Workup

  1. customThe solid product was collected on a filter
  2. washwashed with ether
  3. customdried

Sources & evidence

ORD record
ord-bf7794bac1d84a60a8fc19ba68810e8d
Source dataset
uspto-grants-1983_05
Patent number
US04385104

Reaction notes

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