2-Chloro-5-aminomethylthiazole → HCID 137226484, compound

HRID 1646677Notes

Reaction equation

HRID 1646677 reaction equation
[C:1]([NH:4][C:5](=[N:8][N+:9]([O-:11])=[O:10])SC)(=[O:3])[CH3:2].[NH2:12][CH2:13][C:14]1[S:18][C:17]([Cl:19])=[N:16][CH:15]=1>C(#N)C>[C:1]([NH:4][C:5]([NH:12][CH2:13][C:14]1[S:18][C:17]([Cl:19])=[N:16][CH:15]=1)=[N:8][N+:9]([O-:11])=[O:10])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 101541292-Chloro-5-aminomethylthiazoleHCID 136058307HCID 136058307, compound

Product 1

HCID 137226484HCID 137226484, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 0.22 g of N-acetyl-S-methyl-N'-nitroisothiourea and 5 ml of acetonitrile was dropwise added 0.2 g of 5-(aminomethyl)-2-chlorothiazole at -2° C. Stirring was continued at the same temperature for additional 1 hour, and then the reaction mixture concentrated. The residue solidified was recrystallized from ethanol to give 0.31 g of N-actyl-N'-(2-chloro-5-thiazolylmethyl)-N"-nitroguanidine (reference compound No. 5), mp 132°-133° C. NMR (CDCl3): 2.33(3H, s), 4.68(2H, d, J=6 Hz), 7.50(1H, s), 9.60(1H, br), 11.85(1H, br).

Workup

  1. customat -2° C
  2. concentrationthe reaction mixture concentrated
  3. customThe residue solidified was recrystallized from ethanol

Sources & evidence

ORD record
ord-609b33704eb44770a8689307572cd1ad
Source dataset
uspto-grants-1993_01
Patent number
US05180833

Reaction notes

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