Triethylamine → 2-(o-Chlorophenyl)-3-(3,4-dimethoxyphenyl)-2,3,5,6,7,8-hexahydrothiazolo[3,2-a][1,3]diazepin-3-ol

HRID 67228

반응식

HRID 67228 반응식
[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH:4](O)[C:5](=[O:16])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[NH:34]1[CH2:40][CH2:39][CH2:38][CH2:37][NH:36][C:35]1=[S:41]>CC(C)=O.C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH:4]1[S:41][C:35]2=[N:34][CH2:40][CH2:39][CH2:38][CH2:37][N:36]2[C:5]1([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1)[OH:16]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 7365891,3-Diazepane-2-thioneHCID 150442192-(2-Chlorophenyl)-1-(3,4-dimethoxyphenyl)-2-hydroxyethan-1-one

생성물 1

HCID 130682872-(o-Chlorophenyl)-3-(3,4-dimethoxyphenyl)-2,3,5,6,7,8-hexahydrothiazolo[3,2-a][1,3]diazepin-3-ol

시약·촉매·용매 3

HCID 180Acetone용매2회HCID 962Water용매HCID 1140Toluene용매3회

실험 절차

A 6.13 g. portion of 2'-chloro-3,4-dimethoxybenzoin, 5.6 ml. of triethylamine and 20 ml. of toluene are mixed and stirred. A mixture of 1.55 ml. of methanesulfonyl chloride in 40 ml. of toluene is added over a period of one hour. A 50 ml. portion of water and more toluene are added. The organic layer is separated, washed with water and concentrated in vacuo to give 8.3 g. of 2'-chloro-3,4-dimethoxybenzoin methanesulfonate ester as a viscous oil. A mixture of this oil in 30 ml. of acetone is added to a stirred mixture of 1.95 g. of hexahydro-2H-1,3-diazepine-2-Thione in 150 ml. of acetone. The resulting mixture is stirred for 3 hours, then 3 hours at 45°-50° C., concentrated to 1/3 of its original volume and ether is added producing a gum. The mixture is concentrated free of solvents, 100 ml. of water and 2 ml. of ammonium hydroxide are added and the solid is filtered and washed with water. This solid is dissolved in 20 ml. of ethanol and refrigerated giving 1.3 g. of the desired product, m.p. 98°-100° C.

후처리

  1. additionA mixture of 1.55 ml
  2. customThe organic layer is separated
  3. washwashed with water
  4. concentrationconcentrated in vacuo
  5. customto give 8.3 g
  6. additionA mixture of this oil in 30 ml
  7. stirringThe resulting mixture is stirred for 3 hours
  8. concentration3 hours at 45°-50° C., concentrated to 1/3 of its original volume and ether
  9. additionis added
  10. customproducing a gum
  11. concentrationThe mixture is concentrated free of solvents, 100 ml
  12. additionof ammonium hydroxide are added
  13. filtrationthe solid is filtered
  14. washwashed with water
  15. dissolutionThis solid is dissolved in 20 ml
  16. customof ethanol and refrigerated giving 1.3 g

출처 및 근거

ORD 기록
ord-3dd7ab568a7044628a6fc2869f0d7c63
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04344954

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