Methylamine → 3-iodo-N,4-dimethylbenzamide

HRID 38226Notes

Reaction equation

HRID 38226 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5](Cl)=[O:6].[CH3:12][NH2:13].C1COCC1>C(Cl)Cl>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([NH:13][CH3:12])=[O:6]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 177521573-Iodo-4-methylbenzoyl chloride

Product 1

HCID 196884403-iodo-N,4-dimethylbenzamideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 3-iodo-4-methylbenzoyl chloride (2.80 g; 10.0 mmol) in DCM (10 mL) was slowly added a 2 M solution of methylamine in THF (11 mL, 2.2 eq.). Upon completion of the addition, the ice bath was removed and the mixture was stirred overnight. All volatiles were removed in vacuo and the residue was treated with aq. NaHCO3 (25 mL) and subsequently extracted with ethyl acetate (3×15 mL). The combined organic layers were dried over MgSO4 and evaporated. The target compound 3-iodo-N,4-dimethylbenzamide (2.62 g, 95% yield) was used without further purification.

Workup

  1. additionUpon completion of the addition
  2. customthe ice bath was removed
  3. customAll volatiles were removed in vacuo
  4. additionthe residue was treated with aq. NaHCO3 (25 mL)
  5. extractionsubsequently extracted with ethyl acetate (3×15 mL)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-934d36029049407bbad5704aff0060e1
Source dataset
uspto-grants-2013_09
Patent number
US08524724B2

Reaction notes

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