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

HRID 261419ノート

反応式

HRID 261419 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1c686760680a41f6b5b91615d9118d81
出典データセット
uspto-grants-1979_08
特許番号
US04165378

反応ノート

読み込み中…