Triethylamine → rac-[(5-Chloro-1,3-benzothiazol-2-yl)thio](phenyl)acetic Acid

HRID 1607571

反応式

HRID 1607571 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([SH:10])=[N:7][C:6]=2[CH:11]=1.Br[CH:13]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:14]([OH:16])=[O:15].C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10][CH:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:14]([OH:16])=[O:15])=[N:7][C:6]=2[CH:11]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 97919Bromo(phenyl)acetic acidHCID 178527796HCID 178527796、化合物

生成物 1

HCID 12928398rac-[(5-Chloro-1,3-benzothiazol-2-yl)thio](phenyl)acetic Acid収率 70%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 5-chloro-2-mercaptobenzothiazole (38 g, 0.188 mol) in methylene chloride (750 mL) was added α-bromophenylacetic acid (38 g, 0.177 L mol) and triethylamine (38.5 g, 53 mL, 0.38 mol). The mixture was heated to reflux overnight. The clear solution was evaporated in vacuo and the residue was taken up in ethyl acetate, washed with dilute hydrochloric acid solution, then with water and finally dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo to a small volume and treated with n-hexane whereby the product crystallized out. Filtration yielded the product as a beige crystalline compound (41 g, 70%), m.p. 184°-185° C.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customThe clear solution was evaporated in vacuo
  4. washwashed with dilute hydrochloric acid solution
  5. dry with materialwith water and finally dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo to a small volume
  8. additiontreated with n-hexane whereby the product
  9. customcrystallized out
  10. filtrationFiltration

出典と根拠

ORDレコード
ord-d0a985991e584ee596db388be46e5347
出典データセット
uspto-grants-1989_09
特許番号
US04866082

関連ノート

読み込み中…