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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Methanesulfonyl chloride → 2-(p-Chlorophenyl)-2,3,5,6,7,8-hexahydro-3-[3,4-(methylenedioxy)phenyl]thiazolo[3,2-a][1,3]diazepin-3-ol hydrochloride

HRID 67232
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HRID 67232 반응식
CS([Cl:5])(=O)=O.[Cl:6][C:7]1[CH:25]=[CH:24][C:10]([CH:11](O)[C:12](=[O:22])[C:13]2[CH:18]=[CH:17][C:16]3[O:19][CH2:20][O:21][C:15]=3[CH:14]=2)=[CH:9][CH:8]=1.[NH:26]1[CH2:32][CH2:31][CH2:30][CH2:29][NH:28][C:27]1=[S:33]>CC(C)=O.C1(C)C=CC=CC=1.O.C(N(CC)CC)C>[ClH:5].[Cl:6][C:7]1[CH:25]=[CH:24][C:10]([CH:11]2[S:33][C:27]3=[N:26][CH2:32][CH2:31][CH2:30][CH2:29][N:28]3[C:12]2([C:13]2[CH:18]=[CH:17][C:16]3[O:19][CH2:20][O:21][C:15]=3[CH:14]=2)[OH:22])=[CH:9][CH:8]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 3

HCID 31297Methanesulfonyl chlorideHCID 2235071-(1,3-Benzodioxol-5-yl)-2-(4-chlorophenyl)-2-hydroxyethanoneHCID 7365891,3-Diazepane-2-thione

생성물 1

HCID 205283002-(p-Chlorophenyl)-2,3,5,6,7,8-hexahydro-3-[3,4-(methylenedioxy)phenyl]thiazolo[3,2-a][1,3]diazepin-3-ol hydrochloride

시약·촉매·용매 4

HCID 180Acetone용매2회
HCID 962
Water
용매
HCID 1140Toluene용매3회
HCID 8471Triethylamine용매

실험 절차

A mixture of 1.55 ml. of methanesulfonyl chloride and 40 ml. of toluene is added over a period of one hour to a stirred mixture of 5.8 g. of 4'-chloro-3,4-(methylenedioxy)benzoin, 5.6 ml. of triethylamine and 20 ml. of toluene. The mixture is allowed to stand 4 hours, 50 ml. of water and more toluene are added, the organic layer is separated, washed with water, dried, refrigerated and then concentrated to an oil, giving 8.3 g. of the methanesulfonate ester. This oil is dissolved in 30 ml. of acetone and added to a stirred mixture of 1.95 g. of hexahydro-2H-1,3-diazepin-2-thione in 150 ml. of acetone. The mixture is allowed to stand for 3 hours, heated at 45°-50° C. for 3 hours, refrigerated overnight and concentrated to about 1/3 its original volume. An equal volume of ether is added producing a gum. The solvent is removed, 100 ml. of water and 2 ml. of ammonium hydroxide are added. The solid is collected, washed with water, dried and dissolved in 25 ml. of ethanol. This solution is refrigerated, then filtered and to the filtrate are added alcoholic hydrogen chloride and ether. After refrigeration, the solid is filtered, washed with ether, boiled with 25 ml. of ethanol and filtered. The filtrate is treated with alcoholic hydrogen chloride and cooled, giving 0.41 g. of the desired product, m.p. 184°-186° C.

후처리

  1. additionA mixture of 1.55 ml
  2. customthe organic layer is separated
  3. washwashed with water
  4. customdried
  5. concentrationrefrigerated and then concentrated to an oil
  6. customgiving 8.3 g
  7. dissolutionThis oil is dissolved in 30 ml
  8. waitto stand for 3 hours
  9. temperatureheated at 45°-50° C. for 3 hours, refrigerated overnight
  10. concentrationconcentrated to about 1/3 its original volume
  11. additionAn equal volume of ether is added
  12. customproducing a gum
  13. customThe solvent is removed
  14. additionof ammonium hydroxide are added
  15. customThe solid is collected
  16. washwashed with water
  17. customdried
  18. dissolutiondissolved in 25 ml
  19. filtrationfiltered and to the filtrate
  20. additionare added alcoholic hydrogen chloride and ether
  21. filtrationAfter refrigeration, the solid is filtered
  22. washwashed with ether
  23. filtrationof ethanol and filtered
  24. additionThe filtrate is treated with alcoholic hydrogen chloride
  25. temperaturecooled
  26. customgiving 0.41 g

출처 및 근거

ORD 기록
ord-d4221ef4e3074261a4eed3b243a596f9
출처 데이터셋
uspto-grants-1982_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04344954

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