Phosphorus oxychloride → N'-(2,6-dichloro-4-trifluoromethylphenyl)-chloroacetohydrazonoyl chloride

HRID 8420

Reaction equation

HRID 8420 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Cl:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([Cl:17])[C:8]=1[NH:18][NH:19][C:20](=O)[CH2:21][Cl:22]>C1(C)C=CC=CC=1>[Cl:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([Cl:17])[C:8]=1[NH:18][N:19]=[C:20]([Cl:3])[CH2:21][Cl:22]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 22015908N'-(2,6-dichloro-4-trifluoromethylphenyl)-chloroacetohydrazide

Product 1

HCID 86591113N'-(2,6-dichloro-4-trifluoromethylphenyl)-chloroacetohydrazonoyl chlorideYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

Phosphoryl chloride (500 microlitres, 1.7 equivalents) was added in one portion to a stirred solution of N′-(2,6-dichloro-4-trifluoromethylphenyl)-chloroacetohydrazide (1.0 g, 3.11 mmol) in toluene (20 ml) and heated at 70° C. under an argon atmosphere for 20 hours. The cooled mixture was evaporated and the residue extracted with cyclohexane. The extracts were combined and evaporated to give the title compound (0.971 g) as an orange oil, NMR 4.4 (s, 2H), 7.55 (s, 2H), 7.7 (s, 1H). The yield was 90%.

Workup

  1. customThe cooled mixture was evaporated
  2. extractionthe residue extracted with cyclohexane
  3. customevaporated

Sources & evidence

ORD record
ord-9a91687510384f2a99c8906dc00af77d
Source dataset
uspto-grants-2006_08
Patent number
US07087786B2

Linked notes

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