Tetrahydrofuran → N-(4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)-3-(1-pyrrolyl)phenyl)-2-chloro-5-nitrobenzamide

HRID 719763

Reaction equation

HRID 719763 reaction equation
O1CCCC1.[Cl:6][C:7]1[C:8]([O:17][C:18]2[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][C:19]=2[N:25]2[CH:29]=[CH:28][CH:27]=[CH:26]2)=[N:9][CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1.C(N(CC)CC)C.[Cl:37][C:38]1[CH:46]=[CH:45][C:44]([N+:47]([O-:49])=[O:48])=[CH:43][C:39]=1[C:40](Cl)=[O:41]>O>[Cl:6][C:7]1[C:8]([O:17][C:18]2[CH:24]=[CH:23][C:21]([NH:22][C:40](=[O:41])[C:39]3[CH:43]=[C:44]([N+:47]([O-:49])=[O:48])[CH:45]=[CH:46][C:38]=3[Cl:37])=[CH:20][C:19]=2[N:25]2[CH:29]=[CH:28][CH:27]=[CH:26]2)=[N:9][CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 117637Benzoyl chloride, 2-chloro-5-nitro-HCID 219018824-(3-Chloro-5-trifluoromethyl-2-pyridyloxy)-3-(1-pyrrolyl)aniline

Product 1

HCID 10280324N-(4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)-3-(1-pyrrolyl)phenyl)-2-chloro-5-nitrobenzamideYield 53.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5 mL of a tetrahydrofuran solution comprising 320 mg of 4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)-3-(1-pyrrolyl)aniline and 110 mg of triethylamine, 5 mL of a tetrahydrofuran solution comprising 200 mg of 2-chloro-5-nitrobenzoylchloride was dropwise added, followed by stirring for about 30 minutes, and then water was added, and the precipitated crystals were collected by filtration. The collected crystals were washed with water and then dried to obtain 260 mg of N-(4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)-3-(1-pyrrolyl)phenyl)-2-chloro-5-nitrobenzamide (Compound No. 127) having a melting point of from 165 to 167° C.

Workup

  1. additionwas dropwise added
  2. filtrationthe precipitated crystals were collected by filtration
  3. washThe collected crystals were washed with water
  4. customdried

Sources & evidence

ORD record
ord-871385b06bda4191b3074811150b6d83
Source dataset
uspto-grants-2006_11
Patent number
US07132546B2

Linked notes

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