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 1642462Notes

Reaction equation

HRID 1642462 reaction equation
[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]

Participants

5

Reactant 3

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

Product 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-oneYield 45.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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)+.

Sources & evidence

ORD record
ord-bf8fe468fa5044f98fc2c775c9f1def2
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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