4-Chlorobenzoyl chloride → 2-(3-p-Chlorobenzamido-4-hydroxyphenyl)propionitrile

HRID 2398742Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:13]=[C:14]([CH:19]([CH3:22])[C:20]#[N:21])[CH:15]=[CH:16][C:17]=1[OH:18]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:11][C:12]2[CH:13]=[C:14]([CH:19]([CH3:22])[C:20]#[N:21])[CH:15]=[CH:16][C:17]=2[OH:18])=[O:7])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

p-Chlorobenzoyl chloride (33.25 g; 0.19 mole) was added with cooling during 20 minutes to a stirred solution of 2-(3-amino-4-hydroxyphenyl)propionitrile (28.35 g; 0.175 mole) in dry pyridine (200 ml.) at 0°-3° C. After addition was complete the mixture was heated at 100° C. for one hour. It was then evaporated under reduced pressure to yield crude 2-(3-p-chlorobenzamido-4-hydroxyphenyl)propionitrile as an oil. The oil was boiled for 30 minutes during which time the temperature of the vapour above the oil rose to 130° C. On cooling the residue solidified. Recrystallisation of the solid from methanol yielded 2-(2'-p-chlorophenyl-5'-benzoxazolyl)propionitrile (29.00 g.) m.p. 150°-153° C.

Workup

additionAfter addition
customIt was then evaporated under reduced pressure

Sources & evidence

ORD record: ord-cafd657750b540ddb6f8993598871a36
Source dataset: uspto-grants-1977_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04025636

Reaction notes

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