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

反応式

HRID 67229 の反応式
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

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 180Acetone溶媒HCID 962Water溶媒HCID 1140Toluene溶媒2 回HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7043d8d5037247b294707004144c7972
出典データセット
uspto-grants-1982_08
特許番号
US04344954

関連ノート

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