Tetrahydrofuran → HCID 2671294, compound

HRID 719758Notes

Reaction equation

HRID 719758 reaction equation
O1CCCC1.[O:6]([C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.[Cl:27][C:28]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][C:29]=1[C:30](Cl)=[O:31]>O>[O:6]([C:13]1[CH:14]=[CH:15][C:16]([NH:17][C:30](=[O:31])[C:29]2[CH:33]=[C:34]([N+:37]([O-:39])=[O:38])[CH:35]=[CH:36][C:28]=2[Cl:27])=[CH:18][CH:19]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 8764(4-Aminophenoxy)benzeneHCID 117637Benzoyl chloride, 2-chloro-5-nitro-

Product 1

HCID 2671294HCID 2671294, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into 5 mL of a tetrahydrofuran solution comprising 420 mg of 4-phenoxyaniline and 250 mg of triethylamine, 5 mL of a tetrahydrofuran solution comprising 500 mg of 2-chloro-5-nitrobenzoylchloride was dropwise added under cooling with ice. After stirring for about 30 minutes, water was added thereto, and precipitated crystals were collected by filtration. The collected crystals were washed with water and then dried to obtain 730 mg of N-(4-phenoxyphenyl)-2-chloro-5-nitrobenzamide (Compound No. 27) having a melting point of 128° C.

Workup

  1. additionwas dropwise added
  2. temperatureunder cooling with ice
  3. customprecipitated crystals
  4. filtrationwere collected by filtration
  5. washThe collected crystals were washed with water
  6. customdried

Sources & evidence

ORD record
ord-d834af01c46d421cb9366e1c9b0ed8b1
Source dataset
uspto-grants-2006_11
Patent number
US07132546B2

Reaction notes

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