Hydrochloric Acid → 5(R,S)-methyl-7-sulfamoyl-2,3,4,5-tetrahydrothieno [3,2-f]-1,4-thiazepine

HRID 1197436ノート

反応式

HRID 1197436 の反応式
[Na].[SH:2][CH2:3][CH2:4][NH2:5].[C:6]([C:9]1[CH:10]=[C:11]([S:15]([NH2:18])(=[O:17])=[O:16])[S:12][C:13]=1Cl)(=O)[CH3:7].[BH4-].[Na+].Cl>C(O)C>[CH3:7][CH:6]1[C:9]2[CH:10]=[C:11]([S:15](=[O:17])(=[O:16])[NH2:18])[S:12][C:13]=2[S:2][CH2:3][CH2:4][NH:5]1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 6058CysteamineHCID 4311764Sodium borohydrideHCID 5360545SodiumHCID 191064694-Acetyl-5-chlorothiophene-2-sulfonamide

生成物 1

HCID 571467665(R,S)-methyl-7-sulfamoyl-2,3,4,5-tetrahydrothieno [3,2-f]-1,4-thiazepine収率 85.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

Sodium metal (0.46 g, 0.02 mol) was dissolved in absolute ethanol (50 mL), under a nitrogen atmosphere and 2-mercaptoethylamine (1.55 g, 0.02 mol) was added. After 10 minutes, 4-acetyl-5-chlorothiophene-2-sulfonamide (1.63 g, 0.007 mol) in dry ethanol (70 mL) was added to the reaction and the mixture refluxed for 18 hours. The reaction was cooled to room temperature and sodium borohydride (1.0 g, 0.026 mol) was added. After three hours the reaction mixture was poured into ice water and acidified with 6N HCl. The aqueous solution was extracted with ethyl acetate and the aqueous solution made basic with NaHCO3 and Na2CO3. The product was extracted into ethyl acetate, the extract was dried (Na2SO4), filtered and evaporated. The residue (1.77 g) was crystallized from ethyl acetate-methanol to give analytically pure product (1.58 g, 85%), mp 182°-185° C.

後処理

  1. temperaturethe mixture refluxed for 18 hours
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. extractionThe product was extracted into ethyl acetate
  4. dry with materialthe extract was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue (1.77 g) was crystallized from ethyl acetate-methanol

出典と根拠

ORDレコード
ord-0d68743f52f3493f950331fa6f3fb04d
出典データセット
uspto-grants-1994_01
特許番号
US05276025

反応ノート

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