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

HRID 1153796
Notes
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Reaction equation

HRID 1153796 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 176252-AcetamidothiazoleHCID 201456882-chlorobenzyl-8-trifluoromethyl-4H-1,3-benzoxazin-4-oneHCID 178418339Butyllithium

Product 1

HCID 134230822-(2-chloro-2-phenylacetamido)-beta-oxo-N-(2-thiazolyl)-3-trifluoromethyl-benzene-propanamide

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

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

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

Sources & evidence

ORD record
ord-19429f919282462c93d519f38e68c608
Source dataset
uspto-grants-1984_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04486438

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes