Hydrochloric Acid → HCID 86642818, compound

HRID 1667708Notes

Reaction equation

HRID 1667708 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:5]=[CH:6][C:7]([N+:29]([O-:31])=[O:30])=[C:8]([NH:10][C:11]2[S:12][C:13]([C:26]([NH2:28])=[O:27])=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])[N:15]=2)[CH:9]=1.Cl>C(#N)C>[CH:3]([C:4]1[CH:5]=[CH:6][C:7]([N+:29]([O-:31])=[O:30])=[C:8]([NH:10][C:11]2[S:12][C:13]([C:26]([NH2:28])=[O:27])=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:23])([F:24])[F:25])[N:15]=2)[CH:9]=1)=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866428172-(5-Dimethoxymethyl-2-nitro-phenylamino)-4-(2-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide

Product 1

HCID 86642818HCID 86642818, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.23 g (0.48 mmole) of 2-(5-dimethoxymethyl-2-nitro-phenylamino)-4-(2-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide (VI.17a) in 9 mL mixture of acetonitrile and 2M hydrochloric acid (2:1) was heated at 60 degrees for 3 hours, cooled and concentrated under reduced pressure. The residue was diluted with dichloromethane and saturated sodium bicarbonate. The solid was collected by filtration, washed with water and dried to give 0.14 g of 2-(5-formyl-2-nitro-phenylamino)-4-(2-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide (VI.17b) as an orange solid. The filtrate was extracted twice with dichloromethane. The combined dichloromethane layers were washed with brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure to give additional product of 0.046 g as an orange solid. The combined material was used directly in the next step without further purification.

Workup

  1. temperaturecooled
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with dichloromethane and saturated sodium bicarbonate
  4. filtrationThe solid was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-d3d9e4806cc94012aacbfa48e7041d24
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

Loading…