Hydrochloric Acid → HCID 178439955, compound

HRID 704753Notes

Reaction equation

HRID 704753 reaction equation
[O:1]=[C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[C:13]=1[NH:22][C:23](=O)[CH:24]=[CH:25][CH3:26])[CH2:3][C:4]([NH:6][C:7]1[S:8][CH:9]=[CH:10][N:11]=1)=[O:5].CC(N(C)C)=O.[H-].[Na+].Cl>O>[OH:1][C:2]1[C:12]2[C:13](=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:15]=[CH:16][CH:17]=2)[N:22]=[C:23]([CH:24]=[CH:25][CH3:26])[C:3]=1[C:4]([NH:6][C:7]1[S:8][CH:9]=[CH:10][N:11]=1)=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 31374Dimethylacetamide2×HCID 131715994beta-oxo-2-[(1-oxo-2-butenyl)-amino]-N-(2-thiazolyl)-3-trifluoromethyl-benzene-proponamide

Product 1

HCID 178439955HCID 178439955, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

17.5g of the product of Step A were added to a solution of 175ml of dimethylacetamide and a mixture of 2.11 g of sodium hydride as a 50% dispersion in oil and 100 ml of dimethylacetamide and the mixture was heated at 120° C. for 30 minutes and was then cooled. The mixture was poured into a mixture of water and 2N hydrochloric acid and the mixture was vacuum filtered. The product was washed with water and dried under pressure at 80° C. to obtain 16.7g of 4-hydroxy-2-(1-propenyl)-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline-carboxamide melting at 265° C.

Workup

  1. temperaturewas then cooled
  2. filtrationfiltered
  3. washThe product was washed with water
  4. customdried under pressure at 80° C.

Sources & evidence

ORD record
ord-a2912f4e893048e49ee1b8948ae9fe2b
Source dataset
uspto-grants-1991_01
Patent number
US04988708

Reaction notes

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