Triethylamine → 2-anilino4-methoxy-N-methylbenzamide

HRID 602315Notes

Reaction equation

HRID 602315 reaction equation
[NH:1]([C:8]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN.[CH2:22]([N:24](CC)CC)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CCOC(C)=O.C(Cl)CCl>[NH:1]([C:8]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:9]=1[C:10]([NH:24][CH3:22])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 6364545Methylamine hydrochlorideHCID 126480272-Anilino-4-methoxybenzoic acid

Product 1

HCID 666462242-anilino4-methoxy-N-methylbenzamide

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-anilino-4-methoxybenzoic acid (220 mg), methylamine hydrochloride (100 mg), triethylamine (0.31 mL), EDC (260 mg), and HOBt (210 mg) were combined in 4 mL DMF and stirred overnight at room temp. The reaction was diluted with EtOAc and washed with 10% citric acid (1×), water, and 10% sodium bicarbonate, then dried (Na2SO4) concentrated to give 0.23 g of 2-anilino-4-methoxy-N-methylbenzamide.

Workup

  1. washwashed with 10% citric acid (1×), water, and 10% sodium bicarbonate
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1089c6cb240045799ecc10e4f5bd8737
Source dataset
uspto-grants-2011_03
Patent number
US07906521B2

Reaction notes

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