Acetic Acid → 4-Acetoxy-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide

HRID 653461노트

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HRID 653461 반응식
[OH:1][CH:2]1[CH2:7][CH2:6][S:5](=[O:9])(=[O:8])[C:4]2[S:10][C:11]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:12][C:3]1=2.[C:17](O)(=[O:19])[CH3:18].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.O1CCCC1>[C:17]([O:1][CH:2]1[CH2:7][CH2:6][S:5](=[O:9])(=[O:8])[C:4]2[S:10][C:11]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:12][C:3]1=2)(=[O:19])[CH3:18]

참가 물질

6

반응물 3

HCID 176Acetic Acid2회HCID 10868DicyclohexylcarbodiimideHCID 136170125,6-Dihydro-4-hydroxy-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide

생성물 1

HCID 139116164-Acetoxy-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide수율 111.9%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

5,6-Dihydro-4-hydroxy-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide (2.00 g, 0.0071 m), glacial acetic acid (0.92 g, 0.015 m) and 4-dimethylaminopyridine (0.085 g, 0.0007 m) were dissolved in dry tetrahydrofuran (30 ml) and the solution was cooled to 0° C. under nitrogen and stirred while a solution of dicyclohexylcarbodiimide (1.61 g, 0.0078 m) in dry tetrahydrofuran (10 ml) was added over 10 minutes. After stirring at 0° C. for 1 hour and at ambient temperature for 2 hours, an additional 0.46 g (0.0077 m) of glacial acetic acid was added and stirring was continued at ambient temperature for one hour more. The mixture was filtered and the solid was washed with tetrahydrofuran. The combined filtrate and washings were evaporated in vacuo to give a quantitative yield (2.31 g) of crude product. This material was combined with 1.14 g of identical product from a previous run and chromatographed on silica gel, eluting with 10% methanol-chloroform, to yield 2.57 g (75%) of product. Recrystallization from nitromethane afforded an analytical sample melting at 187.5°-188.5° C.

후처리

  1. additionwas added over 10 minutes
  2. stirringstirring
  3. waitwas continued at ambient temperature for one hour
  4. filtrationThe mixture was filtered
  5. washthe solid was washed with tetrahydrofuran
  6. customThe combined filtrate and washings were evaporated in vacuo
  7. customto give a quantitative yield (2.31 g) of crude product
  8. customchromatographed on silica gel
  9. washeluting with 10% methanol-chloroform

출처 및 근거

ORD 기록
ord-e830d25dbf524e4abb54c33de19f2f6b
출처 데이터셋
uspto-grants-1987_06
특허 번호
US04677115

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