1,3-Dichloroacetone → 4-(Chloromethyl)-2-(thiophen-2-yl)-1,3-oxazole

HRID 322273

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH2:8])=[O:7].[Cl:9][CH2:10][C:11]([CH2:13]Cl)=O.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:9][CH2:10][C:11]1[N:8]=[C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[O:7][CH:13]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2-thiophenecarboxamide (5.09 g) and 1,3-dichloroacetone (457 g) was stirred at 120° C. for 2 hours. The reaction mixture was poured into water, nautralized with potassium carbonate, and then extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fraction eluted with diethyl ether-hexane (1:9, v/v), 4-chloromethyl-2-(2-thienyl)oxazole (4.09 g, 57%) was obtained. Recrystallization from isopropylether gave colorless needles, mp 59-59° C.

Workup

extractionextracted with ethyl acetate
washThe ethyl acetate layer was washed with water
dry with materialdried (MgSO4)
concentrationconcentrated under reduced pressure
washFrom the fraction eluted with diethyl ether-hexane (1:9, v/v)

Sources & evidence

ORD record: ord-c0f2cf7c7df84db1a690d728e4081640
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211215B1

Linked notes

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