Benzoic anhydride → HCID 569822、化合物

HRID 508382ノート

反応式

HRID 508382 の反応式
[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

参加物

6

反応物 4

HCID 7167Benzoic anhydrideHCID 14797Potassium HydroxideHCID 76284hydroxylamine-O-sulfonic acidHCID 178526132HCID 178526132、化合物

生成物 1

HCID 569822HCID 569822、化合物収率 64%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-35b661510ce64db59250a50c8a3bd770
出典データセット
uspto-grants-2015_08
特許番号
US09096504B2

反応ノート

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