Hydrochloric Acid → (E)-N-(2-Chloro-6-methylphenyl)-3-ethoxyacrylamide

HRID 2201976Notes

Reaction equation

NC1S[C:4]([C:7]([NH:9][C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:17])=[O:8])=[CH:5]N=1.[CH2:18]([O:20]C=CC(Cl)=O)[CH3:19].ClC1C=CC=C(C)C=1N.Cl>O1CCCC1.O.N1C=CC=CC=1>[Cl:17][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([CH3:16])[C:10]=1[NH:9][C:7](=[O:8])/[CH:4]=[CH:5]/[O:20][CH2:18][CH3:19]

Participants

Conditions

Temperature: 20 °C

Procedure

PCT Publication No. WO 2005/077945 provides a process for the preparation of 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide (Formula 1c) which involves adding 3-ethoxyacryloyl chloride to a cold stirring solution of 2-chloro-6-methylaniline and pyridine in tetrahydrofuran at a temperature of 0° C. to 5° C. The mixture thus obtained was then warmed, stirred for 2 hours at 20° C., and hydrochloric acid was added at 0° C. to 10° C. The mixture was diluted with water and the resulting solution was concentrated under vacuum to a thick slurry. The slurry was diluted with toluene and stirred for 15 minutes at 20° C. to 22° C. then for 1 hour at 0° C. to obtain (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide.

Workup

customWO 2005/077945 provides a process
customThe mixture thus obtained
temperaturewas then warmed
concentrationthe resulting solution was concentrated under vacuum to a thick slurry
additionThe slurry was diluted with toluene
stirringstirred for 15 minutes at 20° C. to 22° C.

Sources & evidence

ORD record: ord-b764e129ab624b36a971cb67d05d1966
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365526B2

Reaction notes

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