Water → N-Cyclopropyl-3-iodo-4-methylbenzamide

HRID 2354610Notes

Reaction equation

HRID 2354610 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.Cl.CN(C)[CH2:15][CH2:16][CH2:17][N:18]=C=NCC.C1(N)CC1.O>CN(C)C=O>[CH:17]1([NH:18][C:5](=[O:7])[C:4]2[CH:8]=[CH:9][C:10]([CH3:11])=[C:2]([I:1])[CH:3]=2)[CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 69828CyclopropylamineHCID 6216403-Iodo-4-methylbenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 21914546N-Cyclopropyl-3-iodo-4-methylbenzamideYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-iodo-4-methylbenzoic acid (10.5 g, 40 mmol), 1-(3-dimethlaminopropyl)-3-ethylcarbodiimide hydrochloride (9.2 g, 48 mmol) and cyclopropylamine (2.6 g, 45.6 mmol) in N,N-dimethylformamide (70 ml) was stirred at room temperature for 4 h. Water (250 mL) was added. The solution was extracted with ethyl acetate (200 mL×2), washed with saturated K2CO3 solution (200 mL) and water (200 mL). Organic layer was dried over Na2SO4 and evaporated under reduced pressure to give the desired product (11.8 g, 98%).

Workup

  1. extractionThe solution was extracted with ethyl acetate (200 mL×2)
  2. washwashed with saturated K2CO3 solution (200 mL) and water (200 mL)
  3. dry with materialOrganic layer was dried over Na2SO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8d2f94df07fe424f8e935f0838d7f052
Source dataset
uspto-grants-2010_07
Patent number
US07754726B2

Reaction notes

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