Thionyl Chloride → 2-Chloro-1,3-benzoxazol-6-OL

HRID 1276174ノート

反応式

HRID 1276174 の反応式
S[C:2]1[O:3][C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.S(Cl)([Cl:14])=O>CN(C)C=O>[Cl:14][C:2]1[O:3][C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2[N:6]=1

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 178515778HCID 178515778、化合物

生成物 1

HCID 234412462-Chloro-1,3-benzoxazol-6-OL

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-Sulfanyl-1,3-benzoxazol-6-ol (2.08 g) [see Preparation 33] was added to thionyl chloride (12.3 ml), followed by dimethylformamide (0.93 ml). The reaction mixture was heated to reflux for 5 minutes, after which time the mixture was allowed to cool. The solvent was removed under reduced pressure, the residue azeotroped twice with xylene, and the residue then partitioned between diethyl ether and water. The organic layer was separated, dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0 changing to 0:100, by volume, hexane:ethyl acetate in 50% increments to afford 2-chloro-1,3-benzoxazol-6-ol (1.715 g) as a white solid.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 5 minutes
  3. temperatureto cool
  4. customThe solvent was removed under reduced pressure
  5. customthe residue azeotroped twice with xylene
  6. customthe residue then partitioned between diethyl ether and water
  7. customThe organic layer was separated
  8. dry with materialdried over magnesium sulphate
  9. customthe solvent removed under reduced pressure
  10. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0 changing to 0:100, by volume, hexane

出典と根拠

ORDレコード
ord-5ba44b79ebc14144adbcae555f6eda15
出典データセット
uspto-grants-2000_12
特許番号
US06166011

反応ノート

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