Phthalyl-4-isothiocyanate → 5-Isothiocyanato-2-benzofuran-1,3-dione

HRID 1720188ノート

反応式

HRID 1720188 の反応式
[N:1]([C:4]1[CH:5]=[C:6]([C:13]([OH:15])=[O:14])[C:7](=[CH:11][CH:12]=1)[C:8]([OH:10])=O)=[C:2]=[S:3]>FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(Cl)Cl>[N:1]([C:4]1[CH:5]=[C:6]2[C:13](=[O:14])[O:15][C:8](=[O:10])[C:7]2=[CH:11][CH:12]=1)=[C:2]=[S:3]

参加物

4

反応物 1

HCID 191815Phthalyl-4-isothiocyanate

生成物 1

HCID 540346455-Isothiocyanato-2-benzofuran-1,3-dione

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 9845Trifluoroacetic anhydride溶媒

実験手順

The 4-isothiocyanatophthalic acid thus obtained was immediately heated to reflux in a mixture of trifluoroacetic anhydride and methylene chloride for 2 hours under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Recrystallization of the resultant solid from 30 mL of carbon tetrachloride afforded 4-isothiocyanatophthalic anhydride as brownish-purple crystals in a yield of 2.3778 g, (77 percent of theoretical). The title compound melted at 106°-108° C.; 1H NMR (300 MHz, acetone-d6) d, 8.15 (d, J=8.1 Hz, 1H), 8.06 (d, J=1.7 Hz, 1H), 7.97 (dd, J=8.1, 1.7 Hz, 1H); 13C NMR (75 MHz, acetone-d6) d 163.3, 162.6, 139.8, 134.8, 134.6, 130.6, 128.2, 123.5, 111.6; IR (CHCl3) 2010 (br), 1840, 1740 cm-1; MS m/e 205, 161, 133 (base), 74.

後処理

  1. temperaturewas immediately heated
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customRecrystallization of the resultant solid from 30 mL of carbon tetrachloride

出典と根拠

ORDレコード
ord-6170808c89b54db3afbd5bce63188d2e
出典データセット
uspto-grants-1996_04
特許番号
US05505931

反応ノート

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