Phenyl isocyanate → HCID 569822、化合物

HRID 508383ノート

反応式

HRID 508383 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.C1(N=C=O)C=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 7672Phenyl isocyanateHCID 14797Potassium HydroxideHCID 76284hydroxylamine-O-sulfonic acidHCID 178526132HCID 178526132、化合物

生成物 1

HCID 569822HCID 569822、化合物収率 60%

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 room temperature. The white solid (S-benzoylthiohydroxylamine) was collected by filtration and then dissolved in CH2Cl2 (10 mL). To this mixture was added phenyl isocyanate (1.19 g, 10 mmol). The resulting solution was allowed to stir overnight at room temperature. The crude product was collected by the filtration and recrystallized in CH2Cl2/hexane. Pure compound 14 was obtained as a white solid (overall yield 60%). m.p. 184-186° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.11 (s, 1H), 7.99 (s, 1H), 7.88 (d, 7.5 Hz, 2H), 7.74 (t, J=8.1 Hz, 1H), 7.59 (t, J=7.5 Hz, 2H), 7.45 (d, J=7.5 Hz, 2H), 7.24 (t, J=7.8 Hz, 2H), 6.98 (t, J=7.2 Hz, 1H); 13C NMR (75 MHz, DMSO-d6) δ 193.4, 155.0, 140.1, 135.2, 134.6, 130.1, 129.4, 127.2, 123.1, 119.3; IR (thin film) cm−1 3286, 3240, 1697, 1638, 1541, 1474, 1459, 1207; MS m/z 273.1 [M+H]+; calcd for C14H13N2O2S 273.1.

後処理

  1. filtrationThe white solid (S-benzoylthiohydroxylamine) was collected by filtration
  2. dissolutiondissolved in CH2Cl2 (10 mL)
  3. stirringto stir overnight at room temperature
  4. filtrationThe crude product was collected by the filtration
  5. customrecrystallized in CH2Cl2/hexane

出典と根拠

ORDレコード
ord-27b971eee2c54edf8f2b06453e1ca0a7
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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