1,2-Dichloroethane → N-(2-amino-5-carbamoylphenyl)-4-methoxybenzamide

HRID 252822Notes

Reaction equation

HRID 252822 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[NH:11][C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.[NH4+].[Cl-].C(Cl)CCl.CC[N:30](CC)CC>CN(C=O)C>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](=[O:7])[NH2:30])=[CH:4][C:3]=1[NH:11][C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 597368674-Amino-3-(4-methoxybenzamido)benzoic acid

Product 1

HCID 59736879N-(2-amino-5-carbamoylphenyl)-4-methoxybenzamideYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 108 (200 mg, 0.70 mmol), NH4Cl (74 mg, 1.40 mmol), HOBT-hydrate (104 mg, 0.77 mmol), EDC (119 mg, 0.77 mmol) and Et3N (0.29 ml, 2.1 mmol) in DMF (3 ml) was stirred for 16 h at room temperature. The solvent was evaporated, ethyl acetate was added and the organic layer was washed successively with saturated solutions of NH4Cl, NaHCO3 and NaCl, dried over MgSO4, filtered and concentrated. The crude product was triturated in ethyl acetate and filtered to give the title compound 109 (60 mg, 30%). 1H NMR: (DMSO) δ (ppm): 9.57 (s, 1H), 7.96 (d, J=8.8 Hz, 2H), 7.67 (d, J=2.2 Hz, 1H), 7.59 (sb, 1H), 7.52 (dd, J=8.2, 2.0 Hz, 1H), 7.02 (d, J=8.8 Hz, 2H), 6.90 (sb, 1H), 6.72 (d, J=8.4 Hz, 1H), 5.41 (s, 2H), 3.83 (s, 3H). MS: (calc.) 285.1; (obt.) 286.1 (MH)+.

Workup

  1. customThe solvent was evaporated
  2. additionethyl acetate was added
  3. washthe organic layer was washed successively with saturated solutions of NH4Cl, NaHCO3 and NaCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was triturated in ethyl acetate
  8. filtrationfiltered

Sources & evidence

ORD record
ord-3cfb3bde3a114e6b8bd6c702bc945bd4
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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