Triethylamine → HCID 59370537, compound

HRID 554104Notes

Reaction equation

HRID 554104 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]([F:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].O[N:14]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[OH-].[NH4+]>ClCCl>[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]([F:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:14])=[O:5]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 103307052,3-Dichloro-4-fluorobenzoic acid

Product 1

HCID 59370537HCID 59370537, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2,3-dichloro-4-fluorobenzoic acid (0.200 g, 0.92 mmol) in dichloromethane (˜4 ml) was treated with 1-hydroxybenzotriazole (0.162 g, 1.2 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.230 g, 1.2 mmol), and triethylamine (0.56 ml, 4.0 mmol) under argon at room temperature. The mixture was stirred at room temperature for 40 minutes then treated with) 32% aqueous ammonium hydroxide (0.088 ml) and stirred overnight at room temperature. The mixture was diluted with dichloromethane and washed sequentially with water and then with saturated aqueous sodium hydrogen carbonate. The organic layer was separated and dried over sodium sulphate then concentrated to give 2,3-dichloro-4-fluorobenzamide (0.156 g) as a white solid that was used without further purification.

Workup

  1. stirringstirred overnight at room temperature
  2. washwashed sequentially with water
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulphate
  5. concentrationthen concentrated

Sources & evidence

ORD record
ord-bc03d42c624c462889cc9af4286ff00a
Source dataset
uspto-grants-2011_11
Patent number
US08048907B2

Reaction notes

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