Sodium Hydroxide → HCID 14424278, compound

HRID 414223Notes

Reaction equation

HRID 414223 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[S:7][C:8]([CH3:11])=[CH:9][CH:10]=1)=[O:5].[F:12][C:13]([F:24])([F:23])[C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1.[OH-].[Na+]>C(Cl)Cl>[CH3:11][C:8]1[S:7][C:6]([C:4](=[O:5])[CH2:3][NH:2][C:18](=[O:19])[C:17]2[CH:21]=[CH:22][C:14]([C:13]([F:12])([F:23])[F:24])=[CH:15][CH:16]=2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 135833042-Amino-1-(5-methylthiophen-2-yl)ethan-1-one--hydrogen chloride (1/1)2×

Product 1

HCID 14424278HCID 14424278, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of 2-amino-1-(5-methylthienyl)ethanone hydrochloride (3.0 g of a mixture containing approximately 60% 2-amino-1-(5-methylthienyl)ethanone hydrochloride) in methylene chloride (100 ml) was cooled in an ice bath. To this cold mixture was added 4-(trifluoromethyl)benzoyl chloride (2.8 g, 0.013 mole), followed by the slow addition of a 2N solution of sodium hydroxide (9.4 ml). After complete addition, the mixture was stirred at room temperature for three days. The mixture was washed first with an aqueous 5% hydrochloric acid solution, followed by water. The organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure, yielding 3.9 g of N-[2-(5-methylthienyl)-2-oxoethyl]-4-trifluoromethylbenzamide as a solid. A small portion was recrystallized from ethanol for analysis, m.p. 182°-183° C.

Workup

  1. temperaturewas cooled in an ice bath
  2. additionAfter complete addition
  3. washThe mixture was washed first with an aqueous 5% hydrochloric acid solution
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a5933808164b47d0bcc8d79a69af4a7c
Source dataset
uspto-grants-1988_12
Patent number
US04791124

Reaction notes

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