Hydrochloric Acid → 2-(2-chloro-2-phenylacetamido)-beta-oxo-N-(2-thiazolyl)-3-trifluoromethyl-benzene-propanamide

HRID 648734Notes

Reaction equation

C([Li])CCC.[S:6]1[CH:10]=[CH:9][N:8]=[C:7]1[NH:11][C:12](=[O:14])[CH3:13].Cl[C:16]1[CH:37]=[CH:36][CH:35]=[CH:34][C:17]=1[CH2:18][C:19]1[O:20][C:21]2[C:29]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:27]=[CH:26][C:22]=2[C:23](=O)[N:24]=1.[ClH:38].[O:39]1CCCC1>CCCCCC>[Cl:38][CH:18]([C:17]1[CH:16]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:19]([NH:24][C:23]1[C:29]([C:30]([F:31])([F:32])[F:33])=[CH:28][CH:27]=[CH:26][C:22]=1[C:21](=[O:20])[CH2:13][C:12]([NH:11][C:7]1[S:6][CH:10]=[CH:9][N:8]=1)=[O:14])=[O:39]

Participants

Conditions

Temperature: -70 °C

Procedure

28.6 ml of a solution of 1.4 moles of n-butyllithium per liter of hexane were added at 0° C. to a solution of 2.84 g of N-(2-thiazolyl)-acetamide in 100 ml of tetrahydrofuran and 3.39 g of the product of Step A were added to the mixture cooled to -70° C. The mixture was poured into ice and N hydrochloric acid and was extracted with ether. The organic phase was washed successively with N-hydrochloric acid and with water, dried and evaporated to dryness under reduced pressure. The residue was empasted with 50 ml of ether and was vacuum filtered. The product was washed and dried under reduced pressure at 50° C. to obtain 3.2 g of 2-(2-chloro-2-phenylacetamido)-β-oxo-N-(2-thiazolyl)-3-trifluoromethyl-benzenepropanamide melting at 185° C. (decomposition).

Workup

additionwere added to the mixture
extractionwas extracted with ether
washThe organic phase was washed successively with N-hydrochloric acid and with water
customdried
customevaporated to dryness under reduced pressure
filtrationfiltered
washThe product was washed
customdried under reduced pressure at 50° C.

Sources & evidence

ORD record: ord-ed7a1c5592034e3d86487f9563f133db
Source dataset: uspto-grants-1988_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04736033

Reaction notes

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