Acetic Anhydride → 1-Acetyl-1,2-dimethyl-3-nitroisothiourea

HRID 1646679Notes

Reaction equation

HRID 1646679 reaction equation
[CH3:1][NH:2][C:3](=[N:6][N+:7]([O-:9])=[O:8])[S:4][CH3:5].C(=O)([O-])[O-].[K+].[K+].[C:16]([O:19]C(=O)C)(=O)[CH3:17]>C(#N)C>[C:16]([N:2]([CH3:1])[C:3](=[N:6][N+:7]([O-:9])=[O:8])[S:4][CH3:5])(=[O:19])[CH3:17]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 1362270171,2-Dimethyl-3-nitroisothiourea

Product 1

HCID 738660421-Acetyl-1,2-dimethyl-3-nitroisothioureaYield 92.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 1,2-dimethyl-3-nitroisothiourea (2.93 g), potassium carbonate (4.07 g), and acetonitrile (60 ml) was added acetic anhydride (2.53 g) at room temperature and the mixture was stirred for 3 hour at this temperature. Insoluble materials were removed by filtration and the filtrate was concentrated. Chloroform (100 ml) was added to the residue and the mixture was washed with water twice. The chloroform layer was dried over anhydrous magnesium sulfate and concentrated to give 3.48 g of 1-acetyl-1,2-dimethyl-3-nitroisothiourea.

Workup

  1. customInsoluble materials were removed by filtration
  2. concentrationthe filtrate was concentrated
  3. additionChloroform (100 ml) was added to the residue
  4. washthe mixture was washed with water twice
  5. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0d0c809274014a4db1f19b611034964a
Source dataset
uspto-grants-1993_01
Patent number
US05180833

Reaction notes

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