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

HRID 1051178Notes

Reaction equation

HRID 1051178 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>C(Cl)Cl>[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 4-bromo-2-methylbenzoic acid (300 g, 1.4 mol) in DCM (8.4 L) at rt was added cyclopropanamine (79.64 g, 1.4 mol) and EDC (320.9 g, 1.67 mol) in one portion. After stirring overnight, the solution was washed with water and the aqueous phase was reextracted with DCM. 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 (73.4%) 4-bromo-N-cyclopropyl-2-methylbenzamide.

Workup

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

Sources & evidence

ORD record
ord-98789624caf34132b1b8827259709f83
Source dataset
uspto-grants-2016_07
Patent number
US09388140B2

Reaction notes

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