Benzocaine → Ethyl 4-{[3-(4-chlorophenyl)propyl]amino}benzoate

HRID 1703114ノート

反応式

HRID 1703114 の反応式
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.S(O[CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)(=O)(=O)C.CN(C)P(N(C)C)(N(C)C)=O.O1CCCC1>O>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][CH2:19][CH2:18][NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=2)=[CH:22][CH:23]=1

参加物

6

反応物 4

HCID 2337BenzocaineHCID 8028TetrahydrofuranHCID 12679HexamethylphosphoramideHCID 130797053-(4-Chlorophenyl)propyl methanesulfonate

生成物 1

HCID 13079692Ethyl 4-{[3-(4-chlorophenyl)propyl]amino}benzoate

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of 49.5 g. of ethyl 4-aminobenzoate, 34.9 g. of 3-(p-chlorophenyl)propanol O-mesylate in 100 ml. of hexamethylphosphoramide is heated at 125°-130° C. for 16 hours. The solution is diluted with 50 ml. of tetrahydrofuran and with 150 ml. of water. Chilling and filtering gives crystals which are washed with water and recrystallized from ethanol to give 28.3 g. of light yellow crystals. Recrystallizations give the product as crystals, m.p. 122°-124° C.

後処理

  1. additionThe solution is diluted with 50 ml
  2. temperatureChilling
  3. filtrationfiltering
  4. customgives crystals which
  5. washare washed with water
  6. customrecrystallized from ethanol
  7. customto give 28.3 g
  8. customRecrystallizations

出典と根拠

ORDレコード
ord-c88ca0b05d6b434e9ae586b57a0da707
出典データセット
uspto-grants-1982_09
特許番号
US04350822

反応ノート

読み込み中…