Hydrochloric Acid → N-acetyl-N-(2-chloro-5-thiazolylmethyl)-S-methyl-N'-nitroisothiourea

HRID 1939605Notes

Reaction equation

HRID 1939605 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH2:7][NH:8][C:9](=[N:12][N+:13]([O-:15])=[O:14])[S:10][CH3:11])=[CH:5][N:6]=1.[C:16](OC(=O)C)(=[O:18])[CH3:17].Cl>N1C=CC=CC=1>[C:16]([N:8]([CH2:7][C:4]1[S:3][C:2]([Cl:1])=[N:6][CH:5]=1)[C:9](=[N:12][N+:13]([O-:15])=[O:14])[S:10][CH3:11])(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 136331499N-(2-chloro-5-thiazolylmethyl)-S-methyl-N'-nitroisothiourea

Product 1

HCID 70300556N-acetyl-N-(2-chloro-5-thiazolylmethyl)-S-methyl-N'-nitroisothioureaYield 99.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture consisting of 1 g N-(2-chloro-5-thiazolylmethyl)-S-methyl-N'-nitroisothiourea, 1.15 g acetic anhydride and 25 ml pyridine was stirred at room temperature for 3 hours. The reaction mixture was added into an aqueous hydrochloric acid solution (concentrated hydrochloric acid 20 ml, water 50 ml, ice 10 g) for separation into layers. The resultant aqueous layer was extracted with 120 ml of chloroform, while the resultant organic layers were combined together, dried over magnesium sulfate and concentrated to afford 1.15 g of N-acetyl-N-(2-chloro-5-thiazolylmethyl)-S-methyl-N'-nitroisothiourea as a brown crystal, mp 77°-78° C.

Workup

  1. extractionThe resultant aqueous layer was extracted with 120 ml of chloroform
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-21e56d4a93c7494889718320ced1b79f
Source dataset
uspto-grants-1997_12
Patent number
US05696256

Reaction notes

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