Sodium Carbonate → N-carbobenzyloxy-4-(hexadecylamino)benzoyl chloride

HRID 2049091

반응식

HRID 2049091 반응식
[CH2:1]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][CH:19]=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][CH3:16].C(=O)([O-])[O-].[Na+].[Na+].[C:33](Cl)([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34].S(Cl)([Cl:46])=O>O.C(Cl)(Cl)Cl>[C:33]([N:17]([CH2:1][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][CH3:16])[C:18]1[CH:19]=[CH:20][C:21]([C:22]([Cl:46])=[O:24])=[CH:25][CH:26]=1)([O:35][CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:34]

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 24386Thionyl ChlorideHCID 472634-(Hexadecylamino)benzoic acid

생성물 1

HCID 20437379N-carbobenzyloxy-4-(hexadecylamino)benzoyl chloride

시약·촉매·용매 2

HCID 962Water용매HCID 6212Chloroform용매

반응 조건

온도
40 °C

실험 절차

To 15 g. (41.5 m moles) 4-(hexadecylamino)benzoic acid in 200 ml. warm chloroform is added 15 g. sodium carbonate in 150 ml. water. To the vigorously stirred solution is added 10 g. (59 m moles) 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. (5 eq) 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 stirred 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. customThe solvents are evaporated
  9. dissolutionthe residue is dissolved three times in toluene
  10. customevaporating each time
  11. customto yield a viscous, orange oil

출처 및 근거

ORD 기록
ord-719dcf0947bc4e5183450f61378b0a09
출처 데이터셋
uspto-grants-1980_04
특허 번호
US04196208

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