HCID 20144974, compound → HCID 178433180, compound

HRID 648586Notes

Reaction equation

HRID 648586 reaction equation
Br[CH2:2][C:3]([C:5]1[S:9][C:8]([N:10]([CH3:13])[CH:11]=[O:12])=[N:7][C:6]=1[CH3:14])=O.[C:15]([NH:18][C:19]([NH2:21])=[S:20])(=[NH:17])[NH2:16]>CO>[NH:18]([C:19]1[S:20][CH:2]=[C:3]([C:5]2[S:9][C:8]([N:10]([CH3:13])[CH:11]=[O:12])=[N:7][C:6]=2[CH3:14])[N:21]=1)[C:15]([NH2:17])=[NH:16]

Participants

4

Reactant 2

HCID 20144974HCID 20144974, compoundHCID 178513045HCID 178513045, compound

Product 1

HCID 178433180HCID 178433180, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 5-(2-bromoacetyl)-2-(N-methylformamido)-4-methylthiazole (2.77 g) and N-amidinothiourea (2.37 g) in methanol (30 ml) was stirred for 4 hours at ambient temperature and for 60 minutes under refluxing. The reaction mixture was cooled to 5° C. The resulting precipitate was collected by filtration, washed with cold methanol (5 ml×2) and dried under reduced pressure to give 5-(2-guanidinothiazol-4-yl)-2-(N-methylformamido)-4-methylthiazole (2.76 g).

Workup

  1. temperatureunder refluxing
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with cold methanol (5 ml×2)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-ff572eed41e44aa380956fdb1f71e703
Source dataset
uspto-grants-1988_04
Patent number
US04735957

Reaction notes

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