Dicyclohexylcarbodiimide → N-[(2-chlorophenyl)methyl]-N,3-dihydroxy-2,2-dimethylpropanamide

HRID 1995486

反応式

HRID 1995486 の反応式
[OH:1][CH2:2][C:3]([CH3:8])([CH3:7])[C:4](O)=[O:5].[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][NH:17][OH:18].C1(N=C=NC2CCCCC2)CCCCC1>C(O)C.C(Cl)(Cl)Cl>[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][N:17]([OH:18])[C:4](=[O:5])[C:3]([CH3:8])([CH3:7])[CH2:2][OH:1]

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 785483-Hydroxy-2,2-dimethylpropionic acidHCID 12811040N-(2-ChlorobenZyl)hydroxylamine

生成物 1

HCID 13192552N-[(2-chlorophenyl)methyl]-N,3-dihydroxy-2,2-dimethylpropanamide収率 7.9%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6212Chloroform溶媒

実験手順

To a stirred solution of 3.0 grams (0.025 mole) of 3-hydroxy-2,2-dimethylpropionic acid (Example 12, Step A) and 3.9 grams (0.025 mole) of N-(2-chlorophenyl)methyl hydroxylamine (Example 1, Step A-2) in 65 ml of ethanol was added dropwise a solution of 5.2 grams (0.025 mole) of dicyclohexylcarbodiimide in 25 ml of chloroform. Upon completion of addition the reaction mixture was stirred at ambient temperature for 60 hours. The reaction mixture was concentrated under reduced pressure to give a residual solid. The solid was recrystallized from ethanol, then from ethanol-water to give a solid; mp 229°-230°. The filtrates from the recrystallizations were combined and concentrated under high vacuum to give a residual oil. The residual oil was subjected to column chromatography. Elution was accomplished using 4:1--cyclohexane:ethyl acetate. The appropriate fraction was concentrated under reduced pressure to give a solid. The solid was recrystallized from ethyl acetatehexane to give 0.51 gram of N-[(2-chlorophenyl)methyl]-N,3-dihydroxy-2,2-dimethylpropanamide; mp 130°-132°. The solid was recrystallized a second time from ethyl acetate-cyclohexane to raise the mp to 131°-132°.

後処理

  1. additionUpon completion of addition the reaction mixture
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto give a residual solid
  4. customThe solid was recrystallized from ethanol
  5. customfrom ethanol-water to give a solid
  6. customThe filtrates from the recrystallizations
  7. concentrationconcentrated under high vacuum
  8. customto give a residual oil
  9. washElution
  10. concentrationThe appropriate fraction was concentrated under reduced pressure
  11. customto give a solid
  12. customThe solid was recrystallized from ethyl acetatehexane

出典と根拠

ORDレコード
ord-177dedbb92b04e3b949724f14e5ed9a8
出典データセット
uspto-grants-1983_09
特許番号
US04405357

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