Ammonium Hydroxide → 3-iodo-4-methylbenzamide

HRID 1619132Notes

Reaction equation

HRID 1619132 reaction equation
Cl.C[N:3](C)CCCN=C=NCC.O.N1(O)C2C=CC=CC=2N=N1.[OH-].[NH4+].[I:26][C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][C:35]=1[CH3:36])[C:30](O)=[O:31]>CN(C=O)C>[I:26][C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][C:35]=1[CH3:36])[C:30]([NH2:3])=[O:31]

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 6216403-Iodo-4-methylbenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 8333293-iodo-4-methylbenzamideYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (5.49 g, 28.6 mmol), 1H-benzo[d][1,2,3]triazol-1-ol hydrate (3.90 g, 28.9 mmol) and 32% aqueous ammonium hydroxide solution (1.10 mL, 28.7 mmol) were sequentially added to a stirred solution of 3-iodo-4-methylbenzoic acid (5.00 g, 19.1 mmol) in N,N′-dimethylformamide (15 mL) at room temperature. After stirring overnight, the mixture was concentrated in vacuo and water and dichloromethane were added to the mixture. The organic layer was washed with 2N aqueous sodium hydroxide solution, brine, dried (MgSO4) and evaporated to give the title compound (4.34 g, 70%) as a yellow solid.

Workup

  1. concentrationthe mixture was concentrated in vacuo and water and dichloromethane
  2. additionwere added to the mixture
  3. washThe organic layer was washed with 2N aqueous sodium hydroxide solution, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-f45e531ea34f4ed4a834b05c1e81714b
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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