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Hydrochloric Acid → N-methyl-2-(2-phenoxyphenyl)-2-oxoacetamide

HRID 36431
Notes
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Reaction equation

HRID 36431 reaction equation
[CH3:1][NH:2][CH:3]=[O:4].C(N(CC)CC)C.ClC(OC(Cl)=O)(Cl)Cl.[O:20]([C:27]1[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=1[C:29](O)=[O:30])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.S(Cl)(Cl)=O.Cl>C1(C)C=CC=CC=1.O.CC(C)=O>[CH3:1][NH:2][C:3](=[O:4])[C:29]([C:28]1[CH:32]=[CH:33][CH:34]=[CH:35][C:27]=1[O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:30]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10426DiphosgeneHCID 24386Thionyl ChlorideHCID 31254N-MethylformamideHCID 752372-Phenoxybenzoic acid

Product 1

HCID 11780091
N-methyl-2-(2-phenoxyphenyl)-2-oxoacetamide
Yield 61%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
10 °C

Procedure

N-Methylformamide (2.36 g, 40.0 mmol) and triethyl amine (8.08 g, 80.0 mmol) were dissolved in toluene (40 ml). Trichloromethylchloroformate (3.96 g, 20.0 mmol) was added dropwise slowly under ice-cooling while maintaining the inner temperature at 10° C. or lower. The mixture was stirred at the same temperature for 1 hour. A large amount of insoluble materials were precipitated. To the mixture was added 2-phenoxybenzoyl chloride which was prepared from 2-phenoxybenzoic acid (4.28 g, 20.0 mmol) and thionyl chloride (2.86 g, 24.0 mmol). The resulting mixture was stirred at bath temperature of 40° to 50° C. for 26 hours. 5N-Hydrochloric acid (12 ml) and acetone (20 ml) were added, and the mixture was stirred for 12 hours. Water was added to the mixture, which was then extracted with toluene and purified by column chromatography on silica gel to obtain the title compound (3.11 g, Yield: 61.0%).

Workup

  1. temperaturecooling
  2. customA large amount of insoluble materials were precipitated
  3. additionTo the mixture was added 2-phenoxybenzoyl chloride which
  4. stirringThe resulting mixture was stirred at bath temperature of 40° to 50° C. for 26 hours
  5. stirringthe mixture was stirred for 12 hours
  6. extractionwas then extracted with toluene
  7. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3f1a560936404ceab29a4525d3e42212
Source dataset
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05414122

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes