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

HRID 925594Notes

Reaction equation

HRID 925594 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-9e8caff179ef4a60a51502433d4e7cac
Source dataset
uspto-grants-2016_03
Patent number
US09284317B2

Reaction notes

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