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

HRID 2202182
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HRID 2202182 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-27f13c9da1754da5b58e7f2abfc232f8
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365529B2

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