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

HRID 1503364Notes

Reaction equation

HRID 1503364 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 Na2SO4, 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: 1H-NMR (300 MHz, CDCl3): δ=7.34 (s, 1H), 7.27 (d, 1H), 7.14 (d, 1H), 5.96 (bs, 1H), 2.85 (m, 1H), 2.38 (s, 3H), 0.85 (m, 2H), 0.59 (m, 2H) ppm.

Workup

  1. washthe solution was washed with water
  2. dry with materialThe combined organic phases were dried over Na2SO4
  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-48b242de201c468a896a906e9ad09d8e
Source dataset
uspto-grants-2015_12
Patent number
US09212184B2

Reaction notes

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