Benzenesulfonyl chloride → HCID 53909776, compound

HRID 1859727Notes

Reaction equation

HRID 1859727 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6].C(N(CC)CC)C.[C:26]1([S:32](Cl)(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(OCC)(=O)C>[C:26]1([S:32]([NH:1][C:2]2[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=2[O:17][CH3:18])[C:5]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:6])(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chloride2×HCID 84263-Amino-4-methoxybenzanilideHCID 8471Triethylamine2×

Product 1

HCID 53909776HCID 53909776, compoundYield 17.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-amino-4-methoxy-N-phenyl-benzamide (0.9726 g, 4.00 mmol), triethylamine (0.56 mL, 4.02 mmol), and benzenesulfonyl chloride (0.51 mL, 4.00 mmol) in ethyl acetate (70 mL) was heated briefly to obtain a solution. The reaction was stirred overnight at room temperature under nitrogen. An additional equivalent of triethylamine and ½ equivalent of benzenesulfonyl chloride was added and the mixture heated to 50-60° C. After 7 hours, the solvent was removed in vacuo and the residue dissolved in ethyl acetate and washed with 1N HCl followed by saturated NaHCO3. The organic layer was filtered, dried with MgSO4, and stripped of solvent by rotary evaporator. Trituration of the residue in hexane/ethyl acetate (4:1) afforded the product (0.268 g); m.p. 190-194° C.

Workup

  1. temperaturewas heated briefly
  2. customto obtain a solution
  3. temperaturethe mixture heated to 50-60° C
  4. waitAfter 7 hours
  5. customthe solvent was removed in vacuo
  6. dissolutionthe residue dissolved in ethyl acetate
  7. washwashed with 1N HCl
  8. filtrationThe organic layer was filtered
  9. dry with materialdried with MgSO4
  10. customstripped of solvent by rotary evaporator

Sources & evidence

ORD record
ord-fe9fcc0e43be4511a3e2018857990a26
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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