1,2-Dichloroethane → 4-bromo-N-cyclopropyl-2-methylbenzamide

HRID 1773630Notes

Reaction equation

HRID 1773630 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([CH3:11])[CH:3]=1.[CH:12]1([NH2:15])[CH2:14][CH2:13]1.C(Cl)CCl>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:15][CH:12]2[CH2:14][CH2:13]2)=[O:8])=[C:4]([CH3:11])[CH:3]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 69828CyclopropylamineHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 225688404-bromo-N-cyclopropyl-2-methylbenzamideYield 73.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 300 g (1.4 mol) 4-bromo-2-methylbenzoic acid in 8.4 L dichloromethane at 23° C. were added 79.6 g cyclopropanamine and 320.9 g EDC. After stirring overnight, the solution was washed with water and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and evaporated. The remaining solid was triturated with diisopropyl ether, filtered, washed and dried in vaccuo to yield 260 g (73%) of the title compound.

Workup

  1. washthe solution was washed with water
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe remaining solid was triturated with diisopropyl ether
  7. filtrationfiltered
  8. washwashed
  9. customdried in vaccuo

Sources & evidence

ORD record
ord-40eefe4b79b64e60a12b761c319bb5aa
Source dataset
uspto-grants-2016_02
Patent number
US09255100B2

Reaction notes

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