Methyl 4-amino-3-methoxybenzoate → HCID 22041474, compound

HRID 748486Notes

Reaction equation

HRID 748486 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][CH3:13].[Cl:14][C:15]1[CH:28]=[CH:27][C:18]2[S:19][C:20]([S:23](Cl)(=[O:25])=[O:24])=[C:21]([CH3:22])[C:17]=2[CH:16]=1>N1C=CC=CC=1>[Cl:14][C:15]1[CH:28]=[CH:27][C:18]2[S:19][C:20]([S:23]([NH:1][C:2]3[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=3[O:12][CH3:13])(=[O:24])=[O:25])=[C:21]([CH3:22])[C:17]=2[CH:16]=1

Participants

4

Reactant 2

HCID 602411Methyl 4-amino-3-methoxybenzoateHCID 27357565-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chloride

Product 1

HCID 22041474HCID 22041474, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into 4 mL of pyridine were dissolved 120 mg of methyl 4-amino-3-methoxybenzoate and 150 mg of 5-chloro-2-chlorosulfonyl-3-methylbenzo[b]thiophene, followed by 14 hours of stirring at room temperature. After confirmation of disappearance of the starting material, the reaction was terminated by adding water at 0° C., followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation and then the residue was purified by silica gel column chromatography (chloroform/methanol=9/1) to obtain 110 mg of the title compound as colorless amorphous.

Workup

  1. customAfter confirmation of disappearance of the starting material, the reaction was terminated
  2. additionby adding water at 0° C.
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed by evaporation
  7. customthe residue was purified by silica gel column chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-ea346cb5d25b42739462d5593638c21d
Source dataset
uspto-grants-2008_07
Patent number
US07399781B2

Reaction notes

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