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

HRID 1197436노트

반응식

HRID 1197436 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0d68743f52f3493f950331fa6f3fb04d
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05276025

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