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Triethylamine → N-Cbz-N,N-bis(2-chloroethyl)amine

HRID 874569
ノート
印刷プレビュー

反応式

HRID 874569 の反応式
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].Cl.[Cl:13][CH2:14][CH2:15][NH2:16].[Cl:17][CH2:18][CH2:19]N.C(N(CC)CC)C>ClCCl.O1CCCC1>[Cl:13][CH2:14][CH2:15][N:16]([CH2:19][CH2:18][Cl:17])[C:2](=[O:3])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 86583559Bis(2-chloroethylamine) hydrochloride

生成物 1

HCID 12553191N-Cbz-N,N-bis(2-chloroethyl)amine収率 26%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

13.2 ml (92 mmol) of benzyl chloroformate are added slowly to a solution, cooled to 0° C., of 15 g (84 mmol) of bis(2-chloroethylamine) hydrochloride, 26 ml (185 mmol) of triethylamine in 200 ml of dichloromethane and 70 ml of tetrahydrofuran, stirred beforehand for 15 min and then filtered in order to remove the triethylammonium chloride. The reaction medium is stirred at ambient temperature for 18 h. After the addition of water, the reaction medium is extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and evaporated. 20 g of crude residue are obtained and purified by chromatography on silica gel, elution being carried out with an 8/2 heptane/ethyl acetate mixture. 6 g (26%) of benzyl bis(2-chloroethyl)carbamate are thus obtained.

後処理

  1. filtrationfiltered in order
  2. customto remove the triethylammonium chloride
  3. stirringThe reaction medium is stirred at ambient temperature for 18 h
  4. additionAfter the addition of water
  5. extractionthe reaction medium is extracted with ethyl acetate
  6. dry with materialThe organic phase is dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. custom20 g of crude residue are obtained
  10. custompurified by chromatography on silica gel, elution

出典と根拠

ORDレコード
ord-2d1ebec9f9784af0b0e2415325e940b1
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08980897B2

反応ノート

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