Succinic anhydride → HCID 15599104, compound

HRID 986807Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[CH:8]=[C:7]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:6]=1[OH:23])([CH3:4])([CH3:3])[CH3:2].[C:24]1(=[O:30])[O:29][C:27](=[O:28])[CH2:26][CH2:25]1>>[C:1]([C:5]1[CH:10]=[C:9]([N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[C:24]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[O:30])[CH:8]=[C:7]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:6]=1[OH:23])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 7922Succinic anhydride

HCID 15599103HCID 15599103, compound

Product 1

HCID 15599104HCID 15599104, compound

Conditions

Temperature: 140 °C

Procedure

A mixture of 1.50 g (0.0045 mole) of 2,6-di-tertiary-butyl-4-(3'-chloroanilino)phenol and 0.90 g (0.0090 mole) of succinic anhydride was heated under a nitrogen atmosphere at 140° C. for one hour. The resulting solid was recrystallized once from a mixture of ethanol and water and then twice from a mixture of ethyl acetate and hexane to hydroxyphenyl)-N-(3-chlorophenyl)carbamoyl]propionic acid, m.p. 204°-206° C. Analysis: Calculated for C24H30ClNO: % C, 66.7; % H, 7.0; % N, 3.2; Found: % C, 67.1; % H, 7.0; % N, 3.2.

Workup

customThe resulting solid was recrystallized once from a mixture of ethanol and water
additiontwice from a mixture of ethyl acetate and hexane to hydroxyphenyl)-N-(3-chlorophenyl)carbamoyl]propionic acid, m.p. 204°-206° C

Sources & evidence

ORD record: ord-757699abf02540beb9385fa1b7787c0c
Source dataset: uspto-grants-1987_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04716178

Reaction notes

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