Methylamine → 2-Iodo-N-methylbenzamide

HRID 1277905Notes

Reaction equation

HRID 1277905 reaction equation
[CH3:1][NH2:2].[I:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7]>O1CCCC1>[CH3:1][NH:2][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=1[I:3]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 691122-Iodobenzoyl chloride

Product 1

HCID 6158522-Iodo-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A total of 40 ml of a 40% by weight aqueous solution of methylamine was reacted with a solution of 16 g of o-iodobenzoyl chloride in 25 ml of tetrahydrofuran for 10 minutes. The excess solvent was evaporated in a hot water bath at 65°. The mixture was allowed to cool and 40 ml of water was added to precipitate the crude product which was recovered and washed with 1 N NaOH, 1 N HCl, and then water until the washings were neutral. The crude product was dried under vacuum and purified by recrystallization from toluene to yield 12.6 g of N-methyl-o-iodobenzamide as white crystals, m.p. 153°-154°, Rf 0.75 on thin layer chromatography using silica gel 60 and methanolchloroform-acetic acid (15:85:1) mixture.

Workup

  1. customThe excess solvent was evaporated in a hot water bath at 65°
  2. temperatureto cool
  3. addition40 ml of water was added
  4. customto precipitate the crude product which
  5. customwas recovered
  6. washwashed with 1 N NaOH, 1 N HCl
  7. dry with materialThe crude product was dried under vacuum
  8. custompurified by recrystallization from toluene

Sources & evidence

ORD record
ord-e6ed54671a734884ab1b5489352d155b
Source dataset
uspto-grants-1981_07
Patent number
US04279887

Reaction notes

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