Sulfuric Acid → 2-(4-Chlorophenyl)-2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]acetamide

HRID 1250143Notes

Reaction equation

HRID 1250143 reaction equation
[Cl:1][C:2]1[C:3]([CH:12]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C:13]#[N:14])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.S(=O)(=O)(O)[OH:23]>>[C:13]([CH:12]([C:3]1[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][N:4]=1)[C:15]1[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=1)(=[O:23])[NH2:14]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 27738272-(4-Chlorophenyl)-2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]acetonitrile

Product 1

HCID 37609312-(4-Chlorophenyl)-2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]acetamide

Procedure

At 23° C., 6.0 g of 3-chloro-2-[1-(4-chlorophenyl)-1-cyanomethyl]-5-trifluoromethylpyridine (prepared by the method of Example 1) were stirred in 30 ml of 96% strength sulfuric acid for 16 hours. The reaction mixture was then carefully stirred into 200 ml of ice water during which the product crystallized out. The solid was separated off, washed successively with water and n-hexane and dried. Yield: 5.5 g (87%) of colorless crystals; mp.: 135-136° C.

Workup

  1. customcrystallized out
  2. customThe solid was separated off
  3. washwashed successively with water and n-hexane
  4. customdried

Sources & evidence

ORD record
ord-140b324d361d45ab909fc19453a0a708
Source dataset
uspto-grants-2002_01
Patent number
US06337305B1

Reaction notes

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