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

HRID 1044066Notes

Reaction equation

HRID 1044066 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](=O)[CH2:12]Cl>CCOC(C)=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:12]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 220632-Thiophenecarboxamide

Product 1

HCID 25295314-(Chloromethyl)-2-(thiophen-2-yl)-1,3-oxazoleYield 63%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Thiophene-2-carboxamide (0.8 g, 6.29 mmol) and 1,3-dichloropropan-2-one (0.96 g, 7.55 mmol) were heated at 150° C. for 2.5 hours. The dark solid was dissolved in EtOAc and washed with aqueous NaHCO3, then the organic phase was dried over Na2SO4, filtered and evaporated to dryness. The dark brown oil was purified by flash chromatography (Petroleum ether/EtOAc=9/1) to obtain 4-(chloromethyl)-2-(thiophen-2-yl)oxazole (790 mg, 63% yield).

Workup

  1. washwashed with aqueous NaHCO3
  2. dry with materialthe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe dark brown oil was purified by flash chromatography (Petroleum ether/EtOAc=9/1)

Sources & evidence

ORD record
ord-32f419a754234359a1002990a4eba176
Source dataset
uspto-grants-2013_10
Patent number
US08563577B2

Reaction notes

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