Dimethylformamide → HCID 178514602, compound

HRID 280740Notes

Reaction equation

HRID 280740 reaction equation
Br.Br[CH2:3][C:4]([C:6]1[N:7]=[C:8]([NH:11][C:12]([NH2:14])=[NH:13])[S:9][CH:10]=1)=[O:5].[N-:15]=[N+:16]=[N-:17].[Na+].CN(C)C=O.C(=O)([O-])[O-].[Na+].[Na+]>O>[N:15]([CH2:3][C:4]([C:6]1[N:7]=[C:8]([NH:11][C:12]([NH2:14])=[NH:13])[S:9][CH:10]=1)=[O:5])=[N+:16]=[N-:17]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 33557Sodium AzideHCID 178419719HCID 178419719, compound

Product 1

HCID 178514602HCID 178514602, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 50 g (0.14 mol) of 2-bromo-1-(2-guanidino-4-thiazolyl)ethanone hydrobromide, 23.6 g (0.36 mol) of sodium azide, and 250 ml of dimethylformamide was stirred at room temperature for 1.5 hours. The mixture was poured into 1.5 liters of water, and the aqueous solution was made basic with solid sodium carbonate. The resulting precipitate was filtered, washed well with water, and dried, thereby affording 30.6 g (93%) of 2-azido-1-(2-guanidino-4-thiazolyl)-ethanone as a light brown crystalline solid, mp 177° (dec). Analytically pure material can be prepared by recrystallization from absolute ethanol: Calcd. for C6H7N7OS: C, 32.00; H, 3.13; N, 43.53; S. 14.24; found: C, 32.22; H, 3.43; N, 41.93; S, 13.97.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed well with water
  3. customdried

Sources & evidence

ORD record
ord-cac02c8a059946a8885f66db9770b9da
Source dataset
uspto-grants-1986_05
Patent number
US04590299

Reaction notes

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