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

HRID 1982592Notes

Reaction equation

HRID 1982592 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].[CH3:15][O:16][CH2:17][C:18]1[O:23][C:22](=[O:24])[C:21]2[CH:25]=[CH:26][CH:27]=[C:28]([C:29]([F:32])([F:31])[F:30])[C:20]=2[N:19]=1.Cl>O1CCCC1.CCCCCC>[CH3:15][O:16][CH2:17][C:18]([NH:19][C:20]1[C:28]([C:29]([F:30])([F:31])[F:32])=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](=[O:24])[CH2:13][C:12]([NH:11][C:7]1[S:6][CH:10]=[CH:9][N:8]=1)=[O:14])=[O:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 176252-AcetamidothiazoleHCID 133813284H-3,1-Benzoxazin-4-one, 2-(methoxymethyl)-8-(trifluoromethyl)-HCID 178418339Butyllithium

Product 1

HCID 133813462-methoxyacetamido-beta-oxo-N-(2-thiazolyl)-3-trifluoromethyl-benzene-propanamideYield 67.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

150 ml of a solution of 1.5 moles of butyllithium per liter of hexane were added over 20 minutes at 0° C. to a solution of 15.73 g of N-(2-thiazolyl)-acetamide in 550 ml of tetrahydrofuran and the mixture was stirred at 0° C. for 10 minutes and was cooled to -70° C. A solution of 14.4 g of the product of Step A in 165 ml of tetrahydrofuran was added at -70° C. over 15 minutes to the mixture which was then stirred at -70° C. for 30 minutes and poured into a mixture of ice and N hydrochloric acid. The mixture was extracted with ether and the combined organic phases were washed successively with hydrochloric acid and water, dried and evaporated to dryness under reduced pressure at 20° to 30° C. The residue was empasted with 250 ml of ether and was vacuum filtered. The product was washed with ether and dried under reduced pressure at 20° C. to obtain 15 g of 2-methoxyacetamido-β-oxo-N-(2-thiazolyl)-3-trifluoromethyl-benzene-propanamide melting at 152° C.

Workup

  1. temperaturewas cooled to -70° C
  2. stirringwas then stirred at -70° C. for 30 minutes
  3. extractionThe mixture was extracted with ether
  4. washthe combined organic phases were washed successively with hydrochloric acid and water
  5. customdried
  6. customevaporated to dryness under reduced pressure at 20° to 30° C
  7. filtrationfiltered
  8. washThe product was washed with ether
  9. customdried under reduced pressure at 20° C.

Sources & evidence

ORD record
ord-93c6d19745ae4e77af76daeb354dba8f
Source dataset
uspto-grants-1986_06
Patent number
US04596875

Reaction notes

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