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

HRID 2308439노트

반응식

HRID 2308439 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

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 □l, 1.17 mmol) and 2-methoxybenzoyl chloride (136 □l, 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+).

후처리

  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.)

출처 및 근거

ORD 기록
ord-cb21b3cccc95421192821e08239d64c5
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06835732B2

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