HCID 178419747, compound → HCID 178419718, compound

HRID 280743Notes

Reaction equation

HRID 280743 reaction equation
Br.[Br:2][CH2:3][C:4]([C:6]([C:8]1[N:9]=[CH:10][NH:11][CH:12]=1)=[O:7])=O.[C:13]([NH:16][C:17]([NH2:19])=[S:18])(=[NH:15])[NH2:14]>CC(C)=O>[BrH:2].[NH:16]([C:17]1[S:18][CH:3]=[C:4]([C:6]([C:8]2[N:9]=[CH:10][NH:11][CH:12]=2)=[O:7])[N:19]=1)[C:13]([NH2:15])=[NH:14]

Participants

4

Reactant 2

HCID 178419747HCID 178419747, compoundHCID 178513045HCID 178513045, compound

Product 1

HCID 178419718HCID 178419718, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 0.38 g (1.4 mmol) of 2-bromo-1-(4-imidazoyl)ethanone hydrobromide in 10 ml of acetone was warmed until homogeneous, then 0.17 g (1.4 mmol) of amidinothiourea was added and the mixture was heated at reflux for 0.5 hour. The mixture was cooled and the white precipitate was collected, washed with ether, and dried, thereby affording 0.24 g (60%) of 2-guanidino-4-(4-imidazoyl)thiazole hydrobromide, mp 225° (dec). nmr (DMSO-d6) (δ): 8.20 (s, 1H); 8.0 (b, 4H); 7.77 (s, 1H); 7.36 (s, 1H); high resolution mass spectrum: calcd. C7H8N6S: for 208.0531; found: 208.0517; calcd. for C7H8N6S.HBr.H2O: C, 27.37; H, 3.60; N, 27.36; found: C, 27.23; H, 3.57; N, 27.64.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 0.5 hour
  4. temperatureThe mixture was cooled
  5. customthe white precipitate was collected
  6. washwashed with ether
  7. customdried

Sources & evidence

ORD record
ord-922d650cb64241289e428f4eb9116d5a
Source dataset
uspto-grants-1986_05
Patent number
US04590299

Reaction notes

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