Water → AURORA 623

HRID 644000Notes

Reaction equation

HRID 644000 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:14]([O:23][CH3:24])(=[O:22])[C:15]1[C:16](=[CH:18][CH:19]=[CH:20][CH:21]=1)[NH2:17].N1C=CC=CC=1.O>C(Cl)Cl>[CH3:24][O:23][C:14](=[O:22])[C:15]1[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=1[NH:17][S:10]([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 74044-Nitrobenzenesulfonyl chlorideHCID 8635Methyl Anthranilate

Product 1

HCID 721284AURORA 623

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Nitrobenzenesulfonyl chloride (2.22 g, 10 mmol) is added to a solution of methyl anthranilate (1.51 g, 10 mmol) in 20 mL of DCM at RT, followed by slow addition of pyridine (0.97 mL, 12 mmol). The reaction is stirred 16 h at RT. Water (1 mL) is added. After 1 h, the mixture is partitioned between DCM (40 mL) and water (30 mL). The organic phase is washed with water (30 mL) and brine (30 mL), dried over anhydrous magnesium sulfate and concentrated under vacuum to an orange solid. The solid is redissolved in DCM (30 mL), and hexane (100 mL) is added. The solution is concentrated to approximately 60 mL at which point an orange solid rapidly precipitated. The solid is collected by filtration and dried under vacuum to give 2-(4-nitro-benzenesulfonylamino)-benzoic acid methyl ester.

Workup

  1. waitAfter 1 h
  2. customthe mixture is partitioned between DCM (40 mL) and water (30 mL)
  3. washThe organic phase is washed with water (30 mL) and brine (30 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under vacuum to an orange solid
  6. dissolutionThe solid is redissolved in DCM (30 mL)
  7. additionhexane (100 mL) is added
  8. concentrationThe solution is concentrated to approximately 60 mL at which point an orange solid
  9. customrapidly precipitated
  10. filtrationThe solid is collected by filtration
  11. customdried under vacuum

Sources & evidence

ORD record
ord-5b009b26fd5a4451a5969b78f1f7cb7b
Source dataset
uspto-grants-2010_04
Patent number
US07700637B2

Reaction notes

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