Benzocaine → 4-[(11-Phenylundecyl)amino]benzoic acid

HRID 2052481ノート

反応式

HRID 2052481 の反応式
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][CH:3]=1.CS(O[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=O)=O.CN(C)P(N(C)C)(N(C)C)=O>O>[C:29]1([CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:11][CH:12]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

参加物

5

反応物 3

HCID 2337BenzocaineHCID 12679HexamethylphosphoramideHCID 1307969911-Phenyl-1-undecanol O-methanesulfonate

生成物 1

HCID 130796564-[(11-Phenylundecyl)amino]benzoic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 16.5 g. of ethyl p-aminobenzoate, 16.3 g. of 11-phenylundecanol O-methanesulfonate (prepared as described in Example 7) and 50 ml. of hexamethylphosphoramide are heated in an oil bath at 120° C. for 20 hours. The mixture is poured into ice and water and extracted with chloroform. The extracts are washed with water, 0.1 N NaOH, saturated sodium chloride solution and water. After drying over magnesium sulfate the extract is filtered through silica gel and the silica gel is washed with chloroform. The filtrate is concentrated in vacuo to an oil which is combined with 200 ml. of ethanol-water (9:1), 15 g. of potassium hydroxide and the mixture is refluxed for 3.5 hours. The mixture is acidified with concentrated hydrochloric acid, diluted with 50 ml. of water and chilled. Dilution with 100 ml. of ethanol and 25 ml. of water and filtration gives a gummy solid which is washed with water. The solid is dissolved in hexane:ether:ethyl acetate:acetic acid (40:5:5:2) and filtered through silica gel G. The support is washed with the same solvent (2 fractions). The first fraction is concentrated in vacuo to an oil which is crystallized from hexane to give pale yellow crystals, m.p. 50°-52° C. Recrystallization from ether-hexane (1:1) gives white crystals, m.p. 53°-55° C.

後処理

  1. additionA mixture of 16.5 g
  2. extractionextracted with chloroform
  3. washThe extracts are washed with water, 0.1 N NaOH, saturated sodium chloride solution and water
  4. dry with materialAfter drying over magnesium sulfate the extract
  5. filtrationis filtered through silica gel
  6. washthe silica gel is washed with chloroform
  7. concentrationThe filtrate is concentrated in vacuo to an oil which
  8. temperatureof potassium hydroxide and the mixture is refluxed for 3.5 hours
  9. additiondiluted with 50 ml
  10. temperatureof water and chilled
  11. filtrationof water and filtration
  12. customgives a gummy solid which
  13. washis washed with water
  14. dissolutionThe solid is dissolved in hexane:ether:ethyl acetate:acetic acid (40:5:5:2)
  15. filtrationfiltered through silica gel G
  16. washThe support is washed with the same solvent (2 fractions)
  17. concentrationThe first fraction is concentrated in vacuo to an oil which
  18. customis crystallized from hexane
  19. customto give pale yellow crystals, m.p. 50°-52° C
  20. customRecrystallization from ether-hexane (1:1)
  21. customgives white crystals, m.p. 53°-55° C.

出典と根拠

ORDレコード
ord-219cfabf21b44bd49bf34be67bf41a22
出典データセット
uspto-grants-1980_01
特許番号
US04185115

反応ノート

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