Phenylacetyl chloride → S,N-dimethyl-N'-nitro-N-phenylacetylisothiourea

HRID 1657028Notes

Reaction equation

HRID 1657028 reaction equation
[CH3:1][S:2][C:3](=[N:6][N+:7]([O-:9])=[O:8])[NH:4][CH3:5].C(=O)([O-])[O-].[K+].[K+].[C:16]1([CH2:22][C:23](Cl)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC#N>[CH3:1][S:2][C:3](=[N:6][N+:7]([O-:9])=[O:8])[N:4]([CH3:5])[C:23](=[O:24])[CH2:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 11430Potassium CarbonateHCID 1362270171,2-Dimethyl-3-nitroisothiourea

Product 1

HCID 70203144S,N-dimethyl-N'-nitro-N-phenylacetylisothioureaYield 60.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a mixture of S,N-dimethyl-N'-nitroisothiourea (0.5 g), CH3CN (20 ml) and potassium carbonate (0.93 g) was added a solution of phenylacetyl chloride (1.04 g) in CH3CN (2 ml) dropwise at room temperature over 10 minutes under stirring. After stirring for 3 hours, insolubles were filtered off and the filtrate was concentrated in vacuo. The resulting residue was applied to column chromatography on silica gel. The column was eluted with hexaneacetone (2:1) to afford 0.54 g of S,N-dimethyl-N'-nitro-N-phenylacetylisothiourea as an oil.

Workup

  1. stirringAfter stirring for 3 hours
  2. filtrationinsolubles were filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. washThe column was eluted with hexaneacetone (2:1)

Sources & evidence

ORD record
ord-9f632f0f4d9b4c029669f0aac371a93b
Source dataset
uspto-grants-1993_10
Patent number
US05256679

Reaction notes

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