Hydrochloric Acid → HCID 19093385, compound

HRID 487042Notes

Reaction equation

HRID 487042 reaction equation
N1C=CC=CC=1.[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[NH:15][C:16]([C:18]1[N:23]=[C:22](Cl)[CH:21]=[CH:20][CH:19]=1)=[O:17].[OH2:25].[ClH:26].[C:27]1(C)[C:28](C)=[CH:29][CH:30]=[CH:31][CH:32]=1>>[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[NH:15][C:16]([C:18]1[N:23]=[C:22]([O:25][C:32]2[CH:31]=[CH:30][CH:29]=[C:28]([Cl:26])[CH:27]=2)[CH:21]=[CH:20][CH:19]=1)=[O:17]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 1049PyridineHCID 7237O-Xylene2×HCID 19093382HCID 19093382, compound

Product 1

HCID 19093385HCID 19093385, compound

Procedure

A solution of sodium methoxide (from 0.26 g sodium in 10 ml methanol) was added to a solution of 3-chlorophenol (1.4 g) in xylene (20 ml). The solvents were evaporated in vacuo to give the dry sodium phenolate. Pyridine (10 ml) and xylene (20 ml) were added, followed by cuprous chloride (0.3 g) and the mixture heated to reflux. A solution of N-(2,4-difluorophenyl)-2-chloro-6-pyridinecarboxamide (2.6 g) in xylene (10 ml) was added dropwise and the mixture refluxed for a further 13 hours. After cooling, the mixture was poured into water (100 ml) and acidified with dilute hydrochloric acid. The organic phase was separated and the aqueous phase dried over anhydrous magnesium sulphate and evaporated. The residue was purified on a silica gel column using dichloromethane as eluant to give the title compound (2.5 g). Recrystallisation from 40-60 petroleum ether gave the title compound as a white solid of melting point 116°-117° C.

Workup

  1. temperaturethe mixture heated to reflux
  2. temperaturethe mixture refluxed for a further 13 hours
  3. temperatureAfter cooling
  4. customThe organic phase was separated
  5. dry with materialthe aqueous phase dried over anhydrous magnesium sulphate
  6. customevaporated
  7. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-cdef9a34e44649ff9559b4ab59ff34d9
Source dataset
uspto-grants-1994_03
Patent number
US05294597

Reaction notes

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