Hexamethylenetetramine → Benzo(b)thiophene-6-carboxaldehyde

HRID 1007945ノート

反応式

HRID 1007945 の反応式
[CH3:1][C:2]1[C:10]2[CH:9]=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:11][C:12]1[CH:13]=[CH:14][C:15]2[CH:19]=[CH:18][S:17][C:16]=2[CH:20]=1.C(OOC(=O)C1C=CC=CC=1)(=[O:28])C1C=CC=CC=1.BrN1C(=[O:45])CCC1=O.C1N2CN3CN(C2)CN1C3>C1C=CC=CC=1.O.C(O)(=O)C>[S:7]1[CH:8]=[CH:9][C:10]2[C:2]([CH:1]=[O:28])=[CH:3][CH:4]=[CH:5][C:6]1=2.[S:17]1[CH:18]=[CH:19][C:15]2[CH:14]=[CH:13][C:12]([CH:11]=[O:45])=[CH:20][C:16]1=2

参加物

10

反応物 5

HCID 4101HexamethylenetetramineHCID 7187Benzoyl PeroxideHCID 35790MethylbenzothiopheneHCID 67184N-bromobutanimideHCID 84345Benzo(b)thiophene, 4-methyl-

生成物 2

HCID 138740Benzo(b)thiophene-6-carboxaldehydeHCID 13985797Benzo[b]thiophene-4-carboxaldehyde

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 241Benzene溶媒HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

In 350 mL of benzene is dissolved 23.53 g of a mixture of 4-methylbenzo[b]thiophene and 6-methylbenzo[b]thiophene, to which are added 0.77 g of benzoyl peroxide and 39.56 g of N-bromosuccinimide. The mixture thus formed is heated under reflux for 2 hours. After cooling the mixture to 50° C., 70 mL of acetic acid, 70 mL of water and 44.51 g of hexamethylenetetramine are added, and the mixture thus formed is heated under reflux for 2 hours. The solvent is distilled off under reduced pressure, the residue is mixed with water and ethyl acetate, and pH is adjusted to 7.5 with potassium carbonate. The organic layer is separated, washed with water and saturated aqueous solution of sodium chloride successively, and dried over anhydrous magnesium sulfate. The solvent is distilled off under reduced pressure, and the residue is purified by column chromatography (eluent: hexane:ethyl acetate=19:1 to 15:1). Thus, 5.24 g of benzo[b]thiophene-4-carboaldehyde, 5.09 g of benzo[b]thiophene-6-carboaldehyde and 6.71 g of mixture thereof are obtained as oily products.

後処理

  1. customThe mixture thus formed
  2. temperatureis heated
  3. temperatureunder reflux for 2 hours
  4. customthe mixture thus formed
  5. temperatureis heated
  6. temperatureunder reflux for 2 hours
  7. distillationThe solvent is distilled off under reduced pressure
  8. additionthe residue is mixed with water and ethyl acetate, and pH
  9. customThe organic layer is separated
  10. washwashed with water and saturated aqueous solution of sodium chloride successively
  11. dry with materialdried over anhydrous magnesium sulfate
  12. distillationThe solvent is distilled off under reduced pressure
  13. customthe residue is purified by column chromatography (eluent: hexane:ethyl acetate=19:1 to 15:1)

出典と根拠

ORDレコード
ord-0538278b67334cb6b939d5215e9728cf
出典データセット
uspto-grants-2004_09
特許番号
US06797726B1

反応ノート

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