Benzoic anhydride → HCID 569822, compound

HRID 508382Notes

Reaction equation

HRID 508382 reaction equation
[OH-].[K+].[C:3]([OH:11])(=[S:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:12]OS(O)(=O)=O.C(OC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>O>[C:3]([S:10][NH2:12])(=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 7167Benzoic anhydrideHCID 14797Potassium HydroxideHCID 76284hydroxylamine-O-sulfonic acidHCID 178526132HCID 178526132, compound

Product 1

HCID 569822HCID 569822, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of KOH (560 mg, 10 mmol) in water (15 mL) was added thiobenzoic acid (690 mg, 5 mmol) and hydroxylamine-O-sulfonic acid (565 mg, 5 mmol). The solution was stirred for 20 min at rt. The white solid (S-benzoylthiohydroxylamine) was collected by filtration and then dissolved in CH2Cl2 (10 mL). To this mixture was added benzoic anhydride (2.26 g, 10 mmol). The resulting solution was allowed to stir overnight at rt. The crude product was purified by recrystallization (CH2Cl2/hexane) to give 2 as white solid. m.p. 138-140° C.; 1H NMR (300 MHz, CDCl3) δ 7.92 (m, 4H), 7.60 (m, 1H), 7.53 (m, 1H), 7.39 (m, 4H), 7.17 (s, 1H); 13C NMR (75 MHz, CDCl3) δ 190.0, 159.1, 134.6, 134.4, 133.3, 132.8, 129.3, 129.0, 128.0, 127.3; IR (thin film) cm−1 3265, 3062, 1696, 1659, 1451, 1419, 1257, 1207; HRMS m/z 258.0598 [M+H]+; calcd for C14H12NO2S 258.0589; overall yield: 64% (2 steps).

Workup

  1. filtrationThe white solid (S-benzoylthiohydroxylamine) was collected by filtration
  2. dissolutiondissolved in CH2Cl2 (10 mL)
  3. stirringto stir overnight at rt
  4. customThe crude product was purified by recrystallization (CH2Cl2/hexane)

Sources & evidence

ORD record
ord-35b661510ce64db59250a50c8a3bd770
Source dataset
uspto-grants-2015_08
Patent number
US09096504B2

Reaction notes

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