4-Aminobenzoic Acid → HCID 24785947, compound

HRID 2422930Notes

Reaction equation

HRID 2422930 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].C([O-])([O-])=O.[Na+].[Na+].[C:19]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:24]=[CH:23][C:22]([S:25]([O:28][CH2:29][C:30](Cl)=[O:31])(=[O:27])=[O:26])=[CH:21][CH:20]=1>O.C1COCC1.C(OCC)C>[C:19]1([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:24]=[CH:23][C:22]([S:25]([O:28][CH2:29][C:30]([NH:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)=[O:31])(=[O:26])=[O:27])=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 9784-Aminobenzoic AcidHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 86628705HCID 86628705, compound

Product 1

HCID 24785947HCID 24785947, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of p-aminobenzoic acid (43 mg, 0.31 mmol) and NaOH (12.5 mg, 0.31 mmol) in water (3 ml) was stirred at room temperature for 10 min until all of the solid material had dissolved. Na2CO3 (27 mg, 0.258 mmol) was then added and the mixture cooled to 0° C. A suspension of sulfonyl chloride 18 (106 mg, 0.341 mmol) in THF (1 ml) was injected rapidly and the resulting solution allowed to warm to room temperature and stirred for 2 h. Then reaction mixture was poured into a separating funnel containing diethyl ether. The phases were separated and the aqueous phase washed with a further portion of diethyl ether. The aqueous phase was acidified to pH 1 by addition of 1N HCl solution and the product extracted into ethyl acetate. The ethyl acetate was washed twice with 1N HCl solution and the organic phase was dried (Na2SO4), filtered and the solvent removed in vacuo. The resulting solid was recrystallized from hexane/ethyl acetate affording acid 20 as an off white powder (81 mg, 64%). δH (400 MHz, DMSO) 4.79 (2H, s, CH2), 7.45-7.70 (9H, m, ArH), 7.86-8.03 (4H, m, ArH), 10.43 (1H, NH); δc (100.6 MHz, DMSO) 68.2, 119.4, 126.5, 127.9, 128.6, 129.2, 129.6, 129.8, 131.1, 134.3, 138.7, 142.7, 146.7, 164.4, 167.5; MS (ES+) 411.7 (100%, [M+H]+).

Workup

  1. dissolutionhad dissolved
  2. temperaturethe mixture cooled to 0° C
  3. temperatureto warm to room temperature
  4. stirringstirred for 2 h
  5. customThen reaction mixture
  6. additionwas poured into a separating funnel
  7. customThe phases were separated
  8. washthe aqueous phase washed with a further portion of diethyl ether
  9. additionThe aqueous phase was acidified to pH 1 by addition of 1N HCl solution
  10. extractionthe product extracted into ethyl acetate
  11. washThe ethyl acetate was washed twice with 1N HCl solution
  12. dry with materialthe organic phase was dried (Na2SO4)
  13. filtrationfiltered
  14. customthe solvent removed in vacuo
  15. customThe resulting solid was recrystallized from hexane/ethyl acetate affording acid 20 as an off white powder (81 mg, 64%)

Sources & evidence

ORD record
ord-8794540ec7eb4fdfabb93b547f0705c6
Source dataset
uspto-grants-2011_06
Patent number
US07960434B2

Reaction notes

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