Carbon Disulfide → 5-Phenyl-2(3H)-benzoxazolethione

HRID 1815752

反応式

HRID 1815752 の反応式
[C:1](=[S:3])=S.[NH2:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:7][C:6]=1[OH:17].[OH-].[K+]>C(O)C>[C:11]1([C:9]2[CH:8]=[CH:7][C:6]3[O:17][C:1](=[S:3])[NH:4][C:5]=3[CH:10]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

参加物

5

反応物 3

HCID 6348Carbon DisulfideHCID 145622-Amino-4-phenylphenolHCID 14797Potassium Hydroxide

生成物 1

HCID 30326635-Phenyl-2(3H)-benzoxazolethione

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Carbon disulfide (7.7 mL) was added to a mixture of 2-amino-4-phenylphenol (1.0 g, 5.4 mmol), potassium hydroxide (0.36 g, 6.5 mmol) and ethanol (11.7 mL). The flask was fitted with a reflux condenser and the resulting mixture was placed in an oil bath at 60° C. for 16 h. After cooling to RT, the mixture was concentrated and ethyl acetate (20 mL) and 1 M hydrochloric acid (10 mL) were added to the residue. The layers were partitioned and the organic layer was washed successively with 1 M HCl, water and brine. The organic layer was dried (Na2SO4), filtered and concentrated to afford 1.20 g (98%) which was used without further purification: 1H NMR (d6-DMSO, 400 MHz) δ 13.98 (s, 1H), 7.64-7.62 (m, 2H), 7.58-7.49 (m, 2H), 7.46-7.42 (m, 2H), 7.39-7.33 (m, 2H); 13C (d6-DMSO, 400 MHz) δ 181.2, 148.2, 140.1, 138.5, 132.7, 129.7, 128.3, 127.7, 123.4, 111.0, 109.1; MS (Cl) m/z 228.1 (M+1); HPLC retention time=3.09 min.

後処理

  1. customThe flask was fitted with a reflux condenser
  2. concentrationthe mixture was concentrated
  3. additionethyl acetate (20 mL) and 1 M hydrochloric acid (10 mL) were added to the residue
  4. customThe layers were partitioned
  5. washthe organic layer was washed successively with 1 M HCl, water and brine
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford 1.20 g (98%) which
  10. customwas used without further purification

出典と根拠

ORDレコード
ord-8ec2d787cd83457485553c2387aa43c5
出典データセット
uspto-grants-2005_04
特許番号
US06881734B2

関連ノート

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