Formic Acid → N-[2-(Chloroacetyl)phenyl]-N-methylformamide

HRID 358720Notes

Reaction equation

HRID 358720 reaction equation
[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.[Cl:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][CH3:22])=[O:14].C(=O)(O)[O-].[Na+]>ClCCl.O>[Cl:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]([CH3:22])[CH:1]=[O:3])=[O:14]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 198249382-Chloro-1-[2-(methylamino)phenyl]ethanone

Product 1

HCID 23128087N-[2-(Chloroacetyl)phenyl]-N-methylformamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of formic acid (2.3 ml) and acetic anhydride (3.6 ml) was heated at 50 to 60° for 2 hours, cooled to 0 to 5° and dichloromethane (10 ml) added. A solution of 2-chloro-2'-(methylamino)acetophenone (1.6 g) in dichloromethane (25 ml) was added and the solution then stirred at 10°-20° for 3 hours. The solution was cooled to 0 to 5° and water (50 ml) followed by aqueous sodium bicarbonate (1M, 50 ml) was added. The layers were separated and the aqueous layer was extracted with dichloromethane (50 ml). The combined dichloromethane layer and extract were dried over magnesium sulphate and the solvent was removed by distillation to give the novel compound 2'-(2-chloro-acetyl)-N-methylformanilide in the form of an oil.

Workup

  1. temperaturewas heated at 50 to 60° for 2 hours
  2. temperaturecooled to 0 to 5°
  3. temperatureThe solution was cooled to 0 to 5°
  4. additionwas added
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with dichloromethane (50 ml)
  7. extractionThe combined dichloromethane layer and extract
  8. dry with materialwere dried over magnesium sulphate
  9. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-533814242a3344c1aa2444826b05225a
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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