Benzenesulfonyl chloride → HCID 21715919, compound

HRID 1387569Notes

Reaction equation

HRID 1387569 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1OC)[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:36](OCC)(=[O:38])C>>[C:26]1([S:32]([NH:1][C:2]2[C:3]([O:38][CH3:36])=[C:4]([CH:14]=[CH:15][CH:16]=2)[C:5]([NH:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[O:6])(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 4

HCID 7369Benzenesulfonyl chloride2×HCID 84263-Amino-4-methoxybenzanilideHCID 8471Triethylamine2×HCID 8857Ethyl Acetate

Product 1

HCID 21715919HCID 21715919, compound

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 1/2 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-87b391f93cc340368e1fdfa2a8da9ea4
Source dataset
uspto-grants-2001_07
Patent number
US06268387B1

Reaction notes

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