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

HRID 1250143
Notes
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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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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
  • washwashed successively with water and n-hexane
  • customdried
  • Sources & evidence

    ORD record
    ord-140b324d361d45ab909fc19453a0a708
    Source dataset
    uspto-grants-2002_01
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US06337305B1

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes