4-Hydroxybenzaldehyde → 4-(5-Methyl-2-phenyl-4-thiazolylmethoxy)benzaldehyde

HRID 350009Notes

Reaction equation

Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[S:6][C:7]=1[CH3:8].[OH:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:8][C:7]1[S:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:4][C:3]=1[CH2:2][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-chloromethyl-5-methyl-2-phenylthiazole (5.40 g), 4-hydroxybenzaldehyde (2.91 g), anhydrous potassium carbonate (4.95 g) and N,N-dimethylformamide (50 ml) was stirred at 80° C. for 3 hours. The reaction mixture was poured into water, the precipitated solid was collected by filtration, and air-dried to obtain crystals of 4-(5-methyl-2-phenyl-4-thiazolylmethoxy)benzaldehyde (6.85 g, yield 93%). This was recrystallized from ethyl acetate-hexane to obtain colorless prisms. Melting point: 118–119° C.

Workup

filtrationthe precipitated solid was collected by filtration
customair-dried

Sources & evidence

ORD record: ord-549e03a5026d4423a08f028974523830
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179823B1

Reaction notes

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