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

HRID 1646678Notes

Reaction equation

HRID 1646678 reaction equation
[CH3:1][NH:2][C:3](=[N:6][N+:7]([O-:9])=[O:8])[S:4][CH3:5].[C:10]([O:13]C(=O)C)(=O)[CH3:11].Cl>N1C=CC=CC=1>[C:10]([N:2]([CH3:1])[C:3](=[N:6][N+:7]([O-:9])=[O:8])[S:4][CH3:5])(=[O:13])[CH3:11]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 0.50 g of 1,2-dimethyl-3-nitroisothiourea and 10 ml of pyridine was dropwise added 1.03 g of acetic anhydride at room temperature. The mixture was stirred at room temperature for 1 hour, and then poured onto 150 ml of 2N hydrochloric acid followed by extraction with 100 ml of chloroform. The chloroform layer was washed with 50 ml of 2N hydrochloric acid and then concentrated to give 0.60 g of 1-acetyl-1,2-dimethyl-3-nitroisothiourea as pale yellow liquid. NMR (CDCl3):2.23(3H, s), 2.52(3H, s), 3.17(3H, s).

Workup

  1. customat room temperature
  2. extractionfollowed by extraction with 100 ml of chloroform
  3. washThe chloroform layer was washed with 50 ml of 2N hydrochloric acid
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bde128bf18a441f98b7414cfbde53896
Source dataset
uspto-grants-1993_01
Patent number
US05180833

Reaction notes

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