Triethylamine → 2-Methoxy-N-(4-methoxy-7-phenyl-benzothiazol-2-yl)-benzamide

HRID 1062963ノート

反応式

HRID 1062963 の反応式
[NH2:1][C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][CH:8]=[C:7]([O:17][CH3:18])[C:5]=2[N:6]=1.C(N(CC)CC)C.[CH3:26][O:27][C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30](Cl)=[O:31]>C1COCC1.CN(C1C=CN=CC=1)C>[CH3:26][O:27][C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30]([NH:1][C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][CH:8]=[C:7]([O:17][CH3:18])[C:5]=2[N:6]=1)=[O:31]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 889692-Methoxybenzoyl chlorideHCID 222830262-Amino-4-methoxy-7-phenyl-benzothiazole

生成物 1

HCID 222834002-Methoxy-N-(4-methoxy-7-phenyl-benzothiazol-2-yl)-benzamide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 2-amino-4-methoxy-7-phenyl-benzothiazole (200 mg, 0.67 mmol) in THF (10 m) was added DMAP (10 mg, 0.08 mmol), triethylamine (163 □1, 1.17 mmol) and 2-methoxybenzoyl chloride (136 □1, 1 mmol) in THF (2 ml). The mixture was then heated to reflux for 2 h, after cooling, it was partitioned between 1:1 AcOEt/THF (70 ml) and 5% NaHCO3 solution (40 ml). The organic phase was washed with saturated NaCl solution (50 ml), dried with Na2SO4, filtered and the solvent removed under reduced presure. The residue was suspended in ether (10 ml), filtered, washed with ether then dried under vacuum (0.05 mmHg, 60° C.), to afford the title compound was a white solid (260 mg, 85% yield), MS: m/e=390.0 (M+).

後処理

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 2 h
  3. temperatureafter cooling
  4. customit was partitioned between 1:1 AcOEt/THF (70 ml) and 5% NaHCO3 solution (40 ml)
  5. washThe organic phase was washed with saturated NaCl solution (50 ml)
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. customthe solvent removed
  9. filtrationfiltered
  10. washwashed with ether
  11. customthen dried under vacuum (0.05 mmHg, 60° C.)

出典と根拠

ORDレコード
ord-013ebb5218094eb2ba99d3f10dfdc4e9
出典データセット
uspto-grants-2005_11
特許番号
US06963000B2

反応ノート

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