Sodium ethoxide → 2-{(E)-2-[(2-Ethoxyethoxy)-3-methoxyphenyl]-1-ethenyl}-3-(4-trifluoromethyl-phenyl)-4H-benzo[4,5][1,3]thiazolo-[3,2-a]pyrimidin-4-one

HRID 1642462노트

반응식

HRID 1642462 반응식
[CH3:1][C:2]1[N:3]=[C:4]2[N:8]([C:9](=[O:21])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1)[C:7]1[CH:22]=[CH:23][CH:24]=[CH:25][C:6]=1[S:5]2.[CH2:26]([O:28][CH2:29][CH2:30][O:31][C:32]1[C:39]([O:40][CH3:41])=[CH:38][CH:37]=[CH:36][C:33]=1[CH:34]=O)[CH3:27].[O-]CC.[Na+]>C(O)C>[CH2:26]([O:28][CH2:29][CH2:30][O:31][C:32]1[C:39]([O:40][CH3:41])=[CH:38][CH:37]=[CH:36][C:33]=1/[CH:34]=[CH:1]/[C:2]1[N:3]=[C:4]2[S:5][C:6]3[CH:25]=[CH:24][CH:23]=[CH:22][C:7]=3[N:8]2[C:9](=[O:21])[C:10]=1[C:11]1[CH:12]=[CH:13][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:15][CH:16]=1)[CH3:27]

참가 물질

5

반응물 3

HCID 2723922Sodium ethoxideHCID 230098872-(2-Ethoxyethoxy)-3-methoxybenzaldehydeHCID 66753266HCID 66753266, 화합물

생성물 1

HCID 444680842-{(E)-2-[(2-Ethoxyethoxy)-3-methoxyphenyl]-1-ethenyl}-3-(4-trifluoromethyl-phenyl)-4H-benzo[4,5][1,3]thiazolo-[3,2-a]pyrimidin-4-one수율 45.5%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

The title compound was synthesized by condensation of Intermediate 23 (250 mg, 0.690 mmol) with 2-(2-ethoxyethoxy)-3-methoxybenzaldehyde (204 mg, 0.970 mmol) in presence of sodium ethoxide (94 mg, 1.380 mmol) in ethanol (15 ml) according to the procedure outlined in Example 24 to give 178 mg of the desired product as a pale yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 1.91 (t, J=6.9 Hz, 3H), 3.48-3.55 (m, 4H), 3.78 (s, 3H), 4.06 (br s, 2H), 6.81 (d, J=15.6 Hz, 1H), 6.92-6.94 (m, 1H), 7.00-7.02 (m, 1H), 7.55-7.57 (m, 2H), 7.61-7.64 (m, 2H), 7.84-7.87 (m, 2H), 8.07-8.09 (m, 1H), 8.23 (d, J=15.6 Hz, 1H), 8.84-8.87 (m, 1H); ESI-MS (m/z) 567.21 (M+H)+.

출처 및 근거

ORD 기록
ord-bf8fe468fa5044f98fc2c775c9f1def2
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119647B2

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