3-Chlorobenzoic Acid → Thionyl Chloride

HRID 67861

Reaction equation

HRID 67861 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[S:11]([Cl:14])([Cl:13])=[O:12].ClC1C=C(C=CC=1)C(Cl)=O.[NH2:25][C:26]([CH3:30])([CH3:29])[CH2:27]O>>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:7][CH2:27][C:26]([CH3:30])([CH3:29])[N:25]=2)[CH:8]=[CH:9][CH:10]=1.[S:11]([Cl:14])([Cl:13])=[O:12]

Participants

6

Reactant 4

HCID 4473-Chlorobenzoic AcidHCID 118072-Amino-2-methyl-1-propanolHCID 24386Thionyl ChlorideHCID 69252Benzoyl chloride, 3-chloro-

Product 2

HCID 24386Thionyl ChlorideHCID 10798476Oxazole, 2-(3-chlorophenyl)-4,5-dihydro-4,4-dimethyl-

Procedure

2-(3-Chlorophenyl)-4,4-dimethyl-2-oxazoline was prepared from 3-chlorobenzoic acid by reaction with thionyl chloride to give 3-chlorobenzoylchloride, reaction of this acid chloride with 2-amino-2-methylpropanol to give the amide and cyclization of the amide with thionyl chloride followed by neutralization with dilute sodium hydroxide to give 2-(3-chlorophenyl)4,4-dimethyl-2-oxazoline.

Workup

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Sources & evidence

ORD record
ord-13a313c59d624a0f87f4c7f511669bb2
Source dataset
uspto-grants-1982_08
Patent number
US04347178

Linked notes

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