Methanesulfonyl chloride → 2,3,5,6,7,8-Hexahydro-3-(5-methyl-2-thienyl)-2-phenylthiazolo[3,2-a][1,3]diazepin-3-ol

HRID 67229

반응식

HRID 67229 반응식
CS(Cl)(=O)=O.CC1SC([C:12]([C:20]([C:22]([OH:35])([C:29]2[S:30][C:31]([CH3:34])=[CH:32][CH:33]=2)C2C=CC=CC=2)=O)(O)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15]C=2)=CC=1.[NH:36]1[CH2:42][CH2:41][CH2:40][CH2:39][NH:38][C:37]1=[S:43]>CC(C)=O.O.C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH3:34][C:31]1[S:30][C:29]([C:22]2([OH:35])[N:38]3[CH2:39][CH2:40][CH2:41][CH2:42][N:36]=[C:37]3[S:43][CH:20]2[C:12]2[CH:13]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:33][CH:32]=1

참가 물질

8

반응물 3

HCID 31297Methanesulfonyl chlorideHCID 7365891,3-Diazepane-2-thioneHCID 539583875-Methyl-2-thienyl-alpha-hydroxybenzyl ketone

생성물 1

HCID 130682882,3,5,6,7,8-Hexahydro-3-(5-methyl-2-thienyl)-2-phenylthiazolo[3,2-a][1,3]diazepin-3-ol

시약·촉매·용매 4

HCID 180Acetone용매HCID 962Water용매HCID 1140Toluene용매2회HCID 8471Triethylamine용매

실험 절차

A mixture of 1.71 ml. of methanesulfonyl chloride in 40 ml. of toluene is added dropwise to a stirred slurry of 4.65 g. of 5-methyl-2-thienyl-α-hydroxybenzyl ketone and 5.6 ml. of triethylamine in 40 ml. of toluene. The mixture is stirred 20 hours, water is added and the organic layer is separated, washed with water and concentrated to dryness. A 20 ml. portion of ether is added to the residue giving a solid which is collected, washed with ether and dried, giving 4.8 g. of 5-methyl-2-thienyl-α-hydroxybenzyl ketone methanesulfonate ester. A mixture of 2.01 g. of this ester and 0.84 g. of hexahydro-2H-1,3-diazepine-2-thione in 40 ml. of acetone is allowed to stand 48 hours. The solvent is removed, 50 ml. of water and one ml. of concentrated ammonium hydroxide are added and the resulting solid is collected and washed with water. This solid is dissolved in 7 ml. of ethanol and then cooled. The resulting solid is collected, washed with ethanol, then ether and dried in vacuo, giving 1.2 g. of the desired product as a yellow solid, m.p. 70°-90° C.

후처리

  1. additionA mixture of 1.71 ml
  2. customthe organic layer is separated
  3. washwashed with water
  4. concentrationconcentrated to dryness
  5. additionportion of ether is added to the residue
  6. customgiving a solid which
  7. customis collected
  8. washwashed with ether
  9. customdried
  10. customgiving 4.8 g
  11. additionA mixture of 2.01 g
  12. waitto stand 48 hours
  13. customThe solvent is removed
  14. additionof concentrated ammonium hydroxide are added
  15. customthe resulting solid is collected
  16. washwashed with water
  17. dissolutionThis solid is dissolved in 7 ml
  18. temperatureof ethanol and then cooled
  19. customThe resulting solid is collected
  20. washwashed with ethanol
  21. dry with materialether and dried in vacuo
  22. customgiving 1.2 g

출처 및 근거

ORD 기록
ord-7043d8d5037247b294707004144c7972
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04344954

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