Acetic Anhydride → HCID 178485063, compound

HRID 67981Notes

Reaction equation

HRID 67981 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH:8]([C:12]1[S:13][CH:14]=[C:15]([CH2:17][S:18][CH2:19][CH2:20][NH:21][C:22]([NH:26][CH3:27])=[N:23][C:24]#[N:25])[N:16]=1)[C:9]([NH2:11])=[NH:10]>N1C=CC=CC=1.O>[C:5]([N:10]=[C:9]([NH2:11])[NH:8][C:12]1[S:13][CH:14]=[C:15]([CH2:17][S:18][CH2:19][CH2:20][NH:21][C:22]([NH:26][CH3:27])=[N:23][C:24]#[N:25])[N:16]=1)(=[O:7])[CH3:6]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 178485064HCID 178485064, compound

Product 1

HCID 178485063HCID 178485063, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Acetic anhydride (0.39 g.) was added to a stirred suspension of 2-guanidino-4-[2-(2-cyano-3-methylguanidino)ethylthiomethyl]thiazole (1.10 g.) in pyridine (6 ml.) at room temperature. After stirring for two hours, the mixture was diluted with water (50 ml.), extracted with methylene chloride (3×30 ml.) and the combined extracts washed with water (100 ml.) and dried over magnesium sulphate. The solution was filtered and evaporated to dryness to leave a gum which was purified by column chromatography (silica column, eluted with ethyl acetate/ethanol/ammonia (s.g. 0.880) 6:1:1 v/v/v) to give 2-(2-acetylguanidino)-4-[2-(2-cyano-3-methylguanidino)ethylthiomethyl]thiazole as an amorphous solid. The n.m.r. spectrum in d6 dimethyl sulphoxide using tetramethylsilane as internal standard had the following resonances (δ): 2.1 (3H, singlet); 2.7 (5H, multiplet); 3.3 (multiplet, obscured by H2O); 3.7 (2H, singlet); 6.8 (1H, singlet); 7.0 (2H, broad multiplet); 9.0 (2H, very broad) and 10.7 (1H, broad).

Workup

  1. extractionextracted with methylene chloride (3×30 ml.)
  2. washthe combined extracts washed with water (100 ml.)
  3. dry with materialdried over magnesium sulphate
  4. filtrationThe solution was filtered
  5. customevaporated to dryness
  6. customto leave a gum which
  7. customwas purified by column chromatography (silica column, eluted with ethyl acetate/ethanol/ammonia (s.g. 0.880) 6:1:1 v/v/v)

Sources & evidence

ORD record
ord-3f179c1240ab4b01a65c4b499e72d9e6
Source dataset
uspto-grants-1982_08
Patent number
US04347370

Reaction notes

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