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

HRID 1275364Notes

Reaction equation

HRID 1275364 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. 1H-NMR(CDCl3): 7.50 (1H, s), 4.80 (2H, s), 2.52 (3H, s), 2.26 (3H, s)

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-0f0131c3f8ce4e3e9ad4a9655a7c2921
Source dataset
uspto-grants-2000_12
Patent number
US06160126

Reaction notes

Loading…