Acetic Anhydride → N-(6-bromo-1,3-benzothiazol-2-yl)acetamide

HRID 2077488

反応式

HRID 2077488 の反応式
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([NH2:9])[S:8][C:4]=2[CH:3]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([NH:9][C:12](=[O:14])[CH3:13])[S:8][C:4]=2[CH:3]=1

参加物

5

反応物 2

HCID 7918Acetic AnhydrideHCID 851492-Benzothiazolamine, 6-bromo-

生成物 1

HCID 3240669N-(6-bromo-1,3-benzothiazol-2-yl)acetamide収率 103.9%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

6-Bromobenzo[d]thiazol-2-amine (Aldrich, St. Louis, Mo.; 10.02 g, 43.7 mmol) was suspended in DCM (175 mL) to which DMAP (6.107 g, 50.0 mmol) was added. The flask was cooled in an ice water bath under argon, and acetic anhydride (4.60 mL, 48.8 mmol) was added, and the reaction was warmed to RT and stirred overnight. The reaction was washed with 10% HCl and water. The precipitate in the organic phase was filtered. The aqueous washings were extracted with DCM and 10:1 DCM/MeOH. These extracts were concentrated, combined with the filtrate from the above filtration, and concentrated again. The solid was collected (from the filtration as well as the aqueous workup), concentrated, and dried under vacuum to afford the desired N-(6-bromobenzo[d]thiazol-2-yl)acetamide (12.30 g, 45.39 mmol, 88% purity, 91% yield). MS (ESI pos. ion) m/z: 271 (MH+, 79Br), 273 (MH+, 81Br). Calculated exact mass for C9H7BrN2OS: 270 (79Br), 272 (81Br).

後処理

  1. additionwas added
  2. temperatureThe flask was cooled in an ice water bath under argon
  3. washThe reaction was washed with 10% HCl and water
  4. filtrationThe precipitate in the organic phase was filtered
  5. extractionThe aqueous washings were extracted with DCM and 10:1 DCM/MeOH
  6. concentrationThese extracts were concentrated
  7. filtrationcombined with the filtrate from the above filtration
  8. concentrationconcentrated again
  9. customThe solid was collected (
  10. filtrationfrom the filtration as well as the aqueous workup),
  11. concentrationconcentrated
  12. customdried under vacuum

出典と根拠

ORDレコード
ord-71b706d6c0304ad2a4c86fe8a6ccefde
出典データセット
uspto-grants-2011_04
特許番号
US07928140B2

関連ノート

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