3-Nitrobenzaldehyde → 2-{4-[2-(3-Nitrophenyl)-vinyl]-phenyl}-6-methoxybenzothiazole

HRID 339580Notes

Reaction equation

HRID 339580 reaction equation
[O:1]([C:3]1[CH:26]=[CH:25][C:6]2[N:7]=[C:8]([C:10]3[CH:24]=[CH:23][C:13]([CH2:14]P(=O)(OCC)OCC)=[CH:12][CH:11]=3)[S:9][C:5]=2[CH:4]=1)[CH3:2].[N+:27]([C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH:33]=O)([O-:29])=[O:28].C[O-].[Na+]>CO>[N+:27]([C:30]1[CH:31]=[C:32]([CH:33]=[CH:14][C:13]2[CH:12]=[CH:11][C:10]([C:8]3[S:9][C:5]4[CH:4]=[C:3]([O:1][CH3:2])[CH:26]=[CH:25][C:6]=4[N:7]=3)=[CH:24][CH:23]=2)[CH:35]=[CH:36][CH:37]=1)([O-:29])=[O:28]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 10942334Sodium MethoxideHCID 13599215Diethyl 4-(6-methoxybenzothiazol-2-yl)benzylphosphonate

Product 1

HCID 672370082-{4-[2-(3-Nitrophenyl)-vinyl]-phenyl}-6-methoxybenzothiazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared as described in the Alkene Formation section using diethyl 4-(6-methoxyl benzothiazol-2-yl)benzylphosphonate (0.10 g, 0.25 mmol) and 3-nitrobenzaldehyde (0.39 g, 0.25 mmol) in dry MeOH (10 ml) and 0.5 M sodium methoxide (1.02 ml, 0.51 mmol) to give the title compound as (0.079 g, 80%) yellow, feathery crystals after work-up and recrystallisation from CHCl3.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-f08c8753eab543bda6d15ba4889ed857
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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