Hydrogen Bromide → 5-Amino-4-(2-chlorobenzoyl)-3-methyl-1-(2,4,6-trichlorophenyl)pyrazole

HRID 612981Notes

Reaction equation

HRID 612981 reaction equation
ClC1C=CC=CC=1C([NH:6][C:7]1[N:11]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([Cl:19])=[CH:14][C:13]=2[Cl:20])[N:10]=[C:9]([CH3:21])[C:8]=1[C:22](=[O:30])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:29])=O.Br.O>C(O)(=O)C>[NH2:6][C:7]1[N:11]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([Cl:19])=[CH:14][C:13]=2[Cl:20])[N:10]=[C:9]([CH3:21])[C:8]=1[C:22](=[O:30])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:29]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 184277925-(2-Chlorobenzamido)-4-(2-chlorobenzoyl)-3-methyl-1-(2,4,6-trichlorophenyl)pyrazole

Product 1

HCID 129721415-Amino-4-(2-chlorobenzoyl)-3-methyl-1-(2,4,6-trichlorophenyl)pyrazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1.94 g (3.50 mmol of the product of Step B in 20 mL of glacial acetic acid was treated with 20 mL of 48% hydrogen bromide and stirred at reflux for 8 hours. The cooled reaction mixture was treated with water to crystallize the product which was separated by filtration, washed with water and air dried to give the title product, 1.45 g (100%), m.p. softens about 210° C. and melts at 220° C. Anal. Calcd. for C17H11ON3Cl4 : 412.9656. Found: 412.9722.

Workup

  1. temperatureat reflux for 8 hours
  2. customThe cooled reaction mixture
  3. customto crystallize the product which
  4. customwas separated by filtration
  5. washwashed with water and air
  6. customdried

Sources & evidence

ORD record
ord-c1703e5907ef48d18220c5e23fe61648
Source dataset
uspto-grants-1999_12
Patent number
US06005109

Reaction notes

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