Hydrochloric Acid → 3-Chloro-2-[1-(4-chlorophenyl)-1-methoxycarbonyl-methyl]-5-trifluoromethylpyridine

HRID 1250144Notes

Reaction equation

HRID 1250144 reaction equation
Cl.[C:2]([CH:5]([C:13]1[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][N:14]=1)[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)(=[O:4])N.[CH3:24][OH:25]>>[Cl:19][C:18]1[C:13]([CH:5]([C:6]2[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=2)[C:2]([O:25][CH3:24])=[O:4])=[N:14][CH:15]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:17]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 37609312-(4-Chlorophenyl)-2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]acetamide

Product 1

HCID 183272733-Chloro-2-[1-(4-chlorophenyl)-1-methoxycarbonyl-methyl]-5-trifluoromethylpyridine

Procedure

Hydrogen chloride gas was introduced into a solution of 3.0 g of 2-[1-carbamoyl-1-(4-chlorophenyl)methyl]-3-chloro-5-trifluoromethylpyridine (prepared by the method of Example 3) in 100 ml of anhydrous methanol for 5 hours. The mixture was subsequently stirred for another 16 hours and excess hydrogen chloride was removed by passing nitrogen through the mixture. The methanol was separated off and the crude product was purified by silica gel chromatography (eluent: cyclohexane/tert-butyl methyl ether 50:1). Yield: 1.3 g (42%) of colorless crystals; mp.: 103-104° C.

Workup

  1. customexcess hydrogen chloride was removed
  2. customThe methanol was separated off
  3. customthe crude product was purified by silica gel chromatography (eluent: cyclohexane/tert-butyl methyl ether 50:1)

Sources & evidence

ORD record
ord-dc956572f5a94612908079865a8cb83a
Source dataset
uspto-grants-2002_01
Patent number
US06337305B1

Reaction notes

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