Methanol → 2-(2-n-Butylguanidino)-4-[2-(3-methylthioureido)ethylthiomethyl]thiazole

HRID 444006Notes

Reaction equation

HRID 444006 reaction equation
Cl.[CH2:2]([N:6]=[C:7]([NH2:19])[NH:8][C:9]1[S:10][CH:11]=[C:12]([CH2:14][S:15][CH2:16][CH2:17][NH2:18])[N:13]=1)[CH2:3][CH2:4][CH3:5].[CH3:20][N:21]=[C:22]=[S:23].C(N(CC)CC)C.CO>O>[CH2:2]([N:6]=[C:7]([NH2:19])[NH:8][C:9]1[S:10][CH:11]=[C:12]([CH2:14][S:15][CH2:16][CH2:17][NH:18][C:22]([NH:21][CH3:20])=[S:23])[N:13]=1)[CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 11167Methyl isothiocyanateHCID 867366212-(2-n-Butylguanidino)-4-(2-aminoethyl)thiomethylthiazole hydrochloride

Product 1

HCID 541580442-(2-n-Butylguanidino)-4-[2-(3-methylthioureido)ethylthiomethyl]thiazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(2-n-butylguanidino)-4-(2-aminoethyl)thiomethylthiazole hydrochloride (1.10 g.), methylisothiocyanate (0.70 g.), triethylamine (0.90 g.) and methanol (5 ml.) was stirred at room temperature for four hours. It was then diluted with water (25 ml.), extracted with ethyl acetate (2×25 ml.) and the combined extracts washed with water (50 ml.). The organic layer was then extracted with 1 N hydrochloric acid (2×25 ml.), the combined aqueous layers washed with ethyl acetate (25 ml.) and then basified by addition of aqueous ammonia. The resulting emulsion was extracted with ethyl acetate and the extract was washed with water and dried over magnesium sulphate. It was filtered and evaporated to dryness to give 2-(2-n-butylguanidino)-4-[2-(3-methylthioureido)ethylthiomethyl]thiazole as a brown gum. The n.m.r. spectrum in d6 dimethyl sulphoxide (DMSO) using tetramethylsilane as internal standard had the following resonances (δ): 0.6-1.5 (7H, multiplet); 2.5 (2H, multiplet); 2.75 (3H, triplet); 3-3.5 (4H, multiplet); 3.55 (2H, singlet); 6.45 (1H, singlet); 6.7-7.6 (broad multiplet).

Workup

  1. extractionextracted with ethyl acetate (2×25 ml.)
  2. washthe combined extracts washed with water (50 ml.)
  3. extractionThe organic layer was then extracted with 1 N hydrochloric acid (2×25 ml.)
  4. washthe combined aqueous layers washed with ethyl acetate (25 ml.)
  5. additionbasified by addition of aqueous ammonia
  6. extractionThe resulting emulsion was extracted with ethyl acetate
  7. washthe extract was washed with water
  8. dry with materialdried over magnesium sulphate
  9. filtrationIt was filtered
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-4364c9cb7d9a490ba48355e9912023b3
Source dataset
uspto-grants-1981_04
Patent number
US04262126

Reaction notes

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