1,1'-Thiocarbonyldi-2(1H)-pyridone → (2,4-Dichloro-3-isothiocyanato-benzyl)-carbamic acid tert-butyl ester

HRID 410069Notes

Reaction equation

HRID 410069 reaction equation
[C:1](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:2].[C:17]([O:21][C:22](=[O:34])[NH:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([NH2:32])[C:26]=1[Cl:33])([CH3:20])([CH3:19])[CH3:18]>O1CCOCC1>[C:17]([O:21][C:22](=[O:34])[NH:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([N:32]=[C:1]=[S:2])[C:26]=1[Cl:33])([CH3:20])([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 56839980(3-Amino-2,4-dichloro-benzyl)-carbamic acid tert-butyl ester

Product 1

HCID 56840196(2,4-Dichloro-3-isothiocyanato-benzyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1,1′-Thiocarbonyldi-2-pyridone (0.42 g, 1.8 mmol) is added to a mixture of (3-amino-2,4-dichloro-benzyl)-carbamic acid tert-butyl ester (0.50 g, 1.7 mmol) and dioxane (25 mL) and stirred at rt for 2 h and at reflux for 2 d. The mixture is concentrated, diluted with DCM and filtered over silica gel. The filtrate is concentrated to give the title compound.

Workup

  1. temperatureat reflux for 2 d
  2. concentrationThe mixture is concentrated
  3. additiondiluted with DCM
  4. filtrationfiltered over silica gel
  5. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-4498a5eff4f646a08de450efd5209f7b
Source dataset
uspto-grants-2014_06
Patent number
US08759537B2

Reaction notes

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