Thionyl Chloride → 5-Methyl-1,2-oxazole-4-carbonyl chloride

HRID 2086372Notes

Reaction equation

HRID 2086372 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[CH:4][C:3]=1[C:7]([OH:9])=O.O=S(Cl)[Cl:12]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[O:6][N:5]=[CH:4][C:3]=1[C:7]([Cl:12])=[O:9]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14252405-Methylisoxazole-4-carboxylic acid

Product 1

HCID 27599175-Methyl-1,2-oxazole-4-carbonyl chlorideYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
79 °C

Procedure

A mixture of 5-methylisoxazole-4-carboxylic acid (5 g, 39.4 mm), SOCl2 (15 ml, 205.8 mm) and toluene (15 ml) was heated to 79±1° C. and stirred for about 4-5 h. Excess SOCl2 and toluene were evaporated under vacuum (50 torr) at 70° C. to give the title compound (≧99% purity) as a pale yellow liquid residue identical to that of Example 1(a).

Workup

  1. customExcess SOCl2 and toluene were evaporated under vacuum (50 torr) at 70° C.

Sources & evidence

ORD record
ord-3ddabe338b9f47bf8baa0e5c10c5d703
Source dataset
uspto-grants-2004_04
Patent number
US06723855B2

Reaction notes

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