Hydrochloric Acid → HCID 58755293, compound

HRID 1163324Notes

Reaction equation

HRID 1163324 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]2[CH:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:7][O:8][C:4]=2[CH:3]=1.Cl[CH2:17][C:18]1[N:19]=[C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[S:21][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.O>[C:23]1([C:20]2[S:21][CH:22]=[C:18]([CH2:17][O:1][C:2]3[CH:15]=[CH:14][C:5]4[CH:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:7][O:8][C:4]=4[CH:3]=3)[N:19]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2369694-(Chloromethyl)-2-phenyl-1,3-thiazoleHCID 57345855Methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetate

Product 1

HCID 58755293HCID 58755293, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

Methyl (6-hydroxy-2,3-dihydro-1-benzofuran-3-yl)acetate (200 mg, 0.961 mmol) and 4-(chloromethyl)-2-phenyl-1,3-thiazole (240 mg, 1.14 mmol) were dissolved in N,N-dimethylformamide (5 mL), and potassium carbonate (160 mg, 1.16 mmol) was added, and the mixture was stirred at 60-70° C. for 3 hr. Water was added to the reaction mixture, and the mixture was neutralized with 2 M hydrochloric acid. The precipitated crystals were recrystallized from ethyl acetate-diisopropyl ether to give the title compound (270 mg, yield 74%) as colorless prism crystals.

Workup

  1. customThe precipitated crystals were recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-2373a524e6644cd5ae49bba94273ee86
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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