Hydrochloric Acid → 1-Acetyl-1,2-dimethyl-3-nitroisothiourea

HRID 1275365Notes

Reaction equation

HRID 1275365 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].Cl>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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 1362270171,2-Dimethyl-3-nitroisothiourea

Product 1

HCID 738660421-Acetyl-1,2-dimethyl-3-nitroisothioureaYield 93.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of N,S-dimethyl-N'-nitroisothiourea (500 mg), potassium carbonate (695 mg) and acetonitrile (10 ml) was added 376 mg of acetic anhydride at room temperature. After stirring at room temperature for 5 hours, 10 ml of 2N hydrochloric acid was added to the mixture which was then extracted with 40 ml of dichloromethane. The resultant organic layers were washed with aqueous saturated sodium bicarbonate, then dried over anhydrous magnesium sulfate and concentrated to afford 600 mg of N-acetyl-N,S-dimethyl-N'-nitroisothiourea as a white crystal, mp 40-41° C.

Workup

  1. extractionwas then extracted with 40 ml of dichloromethane
  2. washThe resultant organic layers were washed with aqueous saturated sodium bicarbonate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0bfdef418d2e48c085240c4c28980ca2
Source dataset
uspto-grants-2000_12
Patent number
US06160126

Reaction notes

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