1,1'-Thiocarbonyldi-2(1H)-pyridone → tert-Butyl 4-chloro-3-isothiocyanatobenzylcarbamate

HRID 1258625Notes

Reaction equation

HRID 1258625 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[Cl:17])[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[C:18](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:19]>C(Cl)Cl>[Cl:17][C:16]1[CH:15]=[CH:14][C:4]([CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[CH:3][C:2]=1[N:1]=[C:18]=[S:19]

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 22981266Tert-butyl 3-amino-4-chlorobenzylcarbamate

Product 1

HCID 86646335tert-Butyl 4-chloro-3-isothiocyanatobenzylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Tert-butyl 3-amino-4-chlorobenzylcarbamate (2.57 g, 10.0 mmol) was added to a mixture of 1,1′-thiocarbonyldi-2-pyridone (2.55 g, 11.0 mmol) and DCM (90 mL) and it was stirred at rt for 4 h. The mixture was diluted with DCM and filtered over silica gel. The organic layer was concentrated to give the sub-title compound.

Workup

  1. filtrationfiltered over silica gel
  2. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-ac00c7e3e61a4bc3bed2c239964af03c
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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