Ammonium Hydroxide → 2-Amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide

HRID 2201977Notes

Reaction equation

BrNC(=O)CCC(N)=O.[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:12]=1[NH:18][C:19](=[O:25])/[CH:20]=[CH:21]/OCC.[NH2:26][C:27]([NH2:29])=[S:28].[OH-].[NH4+]>O1CCOCC1.O>[NH2:29][C:27]1[S:28][C:20]([C:19]([NH:18][C:12]2[C:13]([CH3:17])=[CH:14][CH:15]=[CH:16][C:11]=2[Cl:10])=[O:25])=[CH:21][N:26]=1

Participants

Conditions

Temperature: 80 °C

Procedure

N-Bromosuccinamide was added to a mixture of (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide in 1,4-dioxane and water at −10° C. to 0° C. to obtain a slurry which was warmed and stirred at 20° C. to 22° C. for 3 hours. Thiourea was added and the mixture was heated to 80° C. After 2 hours, the resulting solution was cooled to 20° C. to 22° C. and concentrated ammonium hydroxide was added dropwise. The resulting slurry was concentrated under vacuum to about half volume and cooled to 0° C. to 5° C. to obtain a solid which was collected by vacuum filtration, washed with cold water, and dried to obtain 2-amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide (Formula 1c).

Workup

customto obtain a slurry which
temperaturewas warmed
waitAfter 2 hours
temperaturethe resulting solution was cooled to 20° C. to 22° C.
concentrationThe resulting slurry was concentrated under vacuum to about half volume
temperaturecooled to 0° C. to 5° C.
customto obtain a solid which
filtrationwas collected by vacuum filtration
washwashed with cold water
customdried

Sources & evidence

ORD record: ord-7402cedab535414992a61ab032e956d8
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365526B2

Reaction notes

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