Benzoic anhydride → HCID 569822, 화합물

HRID 508382노트

반응식

HRID 508382 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 569822HCID 569822, 화합물수율 64%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-35b661510ce64db59250a50c8a3bd770
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096504B2

반응 노트

불러오는 중…