3-Amino-4-methoxybenzanilide → HCID 54135704, compound

HRID 1859755Notes

Reaction equation

HRID 1859755 reaction equation
[C:1]([O:4][C:5]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(O)C(Cl)=O)(=[O:3])[CH3:2].[CH3:16][O:17][C:18]1[CH:32]=[CH:31][C:21]([C:22]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:23])=[CH:20][C:19]=1[NH2:33].C(N(CC)CC)C.[C:41](OCC)(=[O:43])C>>[C:10]1([CH2:5][O:4][C:1](=[O:3])[CH2:2][C:41](=[O:43])[NH:33][C:19]2[CH:20]=[C:21]([C:22](=[O:23])[NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:31]=[CH:32][C:18]=2[O:17][CH3:16])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 4

HCID 84263-Amino-4-methoxybenzanilideHCID 8471TriethylamineHCID 8857Ethyl Acetate2×HCID 54353057HCID 54353057, compound

Product 1

HCID 54135704HCID 54135704, compound

Procedure

Acetoxymandeloyl chloride (1.10 g, 5 mmol) was added to a mixture of 4-methoxy-3-amino-N-phenyl-benzamide (1.24 g, 5 mmol) and triethylamine (1.25 mL, 9 mmol) in ethyl acetate (50 mL). The flask was agitated briefly then allowed to stand overnight at room temperature. The reaction mixture was diluted with ethyl acetate (150 mL), washed with aqueous sodium bicarbonate solution (150 mL) then brine (100 mL), dried over magnesium sulfate, and filtered. Removal of the solvent followed by trituration in hexanes/ethyl acetate (2: 1) gave the product (1.46 g.); m.p. 168-171° C.

Workup

  1. washwashed with aqueous sodium bicarbonate solution (150 mL)
  2. dry with materialbrine (100 mL), dried over magnesium sulfate
  3. filtrationfiltered
  4. customRemoval of the solvent
  5. customgave the product (1.46 g.)

Sources & evidence

ORD record
ord-040821be29874e77bb13ccce21d43ca9
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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