HCID 178432761, compound → HCID 178419245, compound

HRID 1980595Notes

Reaction equation

HRID 1980595 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([C:8](=[O:11])[CH2:9][Br:10])=[C:5]([CH3:7])[N:6]=1.[C:12]([NH:15][C:16]([NH2:18])=[S:17])(=[NH:14])[NH2:13]>CC(C)=O>[OH2:11].[BrH:10].[NH:15]([C:16]1[S:17][CH:9]=[C:8]([C:4]2[NH:3][C:2]([CH3:1])=[N:6][C:5]=2[CH3:7])[N:18]=1)[C:12]([NH2:14])=[NH:13].[NH:15]([C:16]1[S:17][CH:9]=[C:8]([C:4]2[NH:3][C:2]([CH3:1])=[N:6][C:5]=2[CH3:7])[N:18]=1)[C:12]([NH2:14])=[NH:13].[BrH:10]

Participants

4

Reactant 2

HCID 178432761HCID 178432761, compoundHCID 178513045HCID 178513045, compound

Product 1

HCID 178419245HCID 178419245, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 1.0 g (4.6 mmol) of 1-(2,4-dimethyl-5-imidazolyl)-2-bromoethanone in 50 ml of acetone was warmed and 0.55 g (4.6 mmol) of amidinothiourea was added. The mixture was heated at reflux for 1 hour, during which time a white solid precipitated. The precipate was collected, washed with acetone, and dried to give 1.12 g (77%) of 2-guanidino-4-(2,4-dimethyl-5-imidazolyl)thiazole hydrobromide hemihydrate as a white solid, mp 273° (dc). nmr (D6DMSO) (δ): 8.4-7.2 (b, 7H); 7.00 (s, 1H); 2.50 (s, 3H); 2.38 (s, 3H). Anal. Calcd. for C7H12N6S.HBr.1/2H2O: C, 33.14; H, 4.33; N, 25.76; S. 9.83. Found: C, 33.47; H, 4.19; N, 25.93; S, 9.91.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour, during which time a white solid
  3. customprecipitated
  4. customThe precipate was collected
  5. washwashed with acetone
  6. customdried

Sources & evidence

ORD record
ord-af4541a5b3424ac1878cee58887505e0
Source dataset
uspto-grants-1985_04
Patent number
US04510313

Reaction notes

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