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Chloroform → N-Carbobenzyloxy-4-(16-bromohexadecylamino)benzoyl chloride

HRID 1106153
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HRID 1106153 반응식
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=O)=[CH:21][CH:20]=1.C(Cl)(Cl)[Cl:29].C(=O)([O-])[O-].[Na+].[Na+].[C:38](Cl)([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39]>O>[C:38]([N:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])[C:19]1[CH:20]=[CH:21][C:22]([C:23]([Cl:29])=[O:25])=[CH:26][CH:27]=1)([O:40][CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)=[O:39]
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참가 물질

6

반응물 4

HCID 6212ChloroformHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 204825194-(16-Bromohexadecylamino)benzoic acid

생성물 1

HCID 20482544N-Carbobenzyloxy-4-(16-bromohexadecylamino)benzoyl chloride

시약·촉매·용매 1

HCID 962Water용매

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온도
40 °C

실험 절차

To 15 g. 4-(16-bromohexadecylamino)benzoic acid in 200 ml. warm chloroform is added 15 g. sodium carbonate in 150 ml. water. To the vigorously solution is added 10 g. carbobenzyloxy chloride. After 2 hours stirring at 40° C., the layers are separated, washed three times with 1 N hydrochloric acid dried, and evaporated to an oil. The oil is dissolved in 300 ml. toluene, treated with 15 ml. thionyl chloride and the solution is refluxed for 5 hours. The solvents are evaporated and the residue is dissolved three times in toluene, evaporating each time to yield a viscous, orange oil.

후처리

  1. additionTo the vigorously solution is added 10 g
  2. customthe layers are separated
  3. washwashed three times with 1 N hydrochloric acid
  4. customdried
  5. customevaporated to an oil
  6. dissolutionThe oil is dissolved in 300 ml
  7. additiontoluene, treated with 15 ml
  8. temperaturethionyl chloride and the solution is refluxed for 5 hours
  9. customThe solvents are evaporated
  10. dissolutionthe residue is dissolved three times in toluene
  11. customevaporating each time
  12. customto yield a viscous, orange oil

출처 및 근거

ORD 기록
ord-03430be076024992b5884d09881ed675
출처 데이터셋
uspto-grants-1982_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04311846

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