1,2-Dimethoxyethane → 2-[4-(Hexadecylamino)phenyl]oxazoline

HRID 2163788

반응식

HRID 2163788 반응식
Br.Br[CH2:3][CH2:4][NH2:5].C(COC)OC.Cl.[CH2:13]([NH:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[CH2:13]([NH:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]2[O:35][CH2:3][CH2:4][N:5]=2)=[CH:32][CH:31]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

참가 물질

6

반응물 3

HCID 80711,2-Dimethoxyethane2회HCID 27742172-Bromoethylamine hydrobromideHCID 132553224-Hexadecylaminobenzoyl chloride hydrochloride

생성물 1

HCID 204373702-[4-(Hexadecylamino)phenyl]oxazoline

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8471Triethylamine용매

실험 절차

To a slurry of 15 g. of 2-bromoethylamine hydrobromide in 150 ml. of glyme was added simultaneously solutions of 31 g. of 4-(hexadecylamino)benzoyl chloride hydrochloride in 60 ml. of glyme and 50 cc. of triethylamine (dropwise). Upon addition of 0.5 g. of 4-dimethylaminopyridine the "solution" was stirred at room temperature overnight. The solution was refluxed for one hour and filtered. The solid was oven dried and portitioned between CH2Cl and water. The layers were separated and the organic phase dried over MgSO4. The organic layer was concentrated to about 100 ml. and 4-(hexadecylamino)benzoyl chloride hydrochloride diluted with an equal volume of hexane. The combined product (4.15 g.) was preabsorbed on 40 g. of silica III and placed on a column of silica III (800 g.). Fractions were collected by U.V. (CH2Cl2 --EtOH 97-3) and samples with the same TLC combined giving 3.8 g. after recrystallization from cyclohexane. A 210 mg. sample was recrystallized from acetonitrile and CH2Cl2 /hexane giving 149 mg., m.p. 123°-125° C.

후처리

  1. additionUpon addition of 0.5 g
  2. temperatureThe solution was refluxed for one hour
  3. filtrationfiltered
  4. customdried
  5. customThe layers were separated
  6. dry with materialthe organic phase dried over MgSO4
  7. concentrationThe organic layer was concentrated to about 100 ml
  8. additionand 4-(hexadecylamino)benzoyl chloride hydrochloride diluted with an equal volume of hexane
  9. customThe combined product (4.15 g.) was preabsorbed on 40 g
  10. customFractions were collected by U.V
  11. custom(CH2Cl2 --EtOH 97-3) and samples with the same TLC combined giving 3.8 g
  12. customafter recrystallization from cyclohexane
  13. customsample was recrystallized from acetonitrile and CH2Cl2 /hexane giving 149 mg

출처 및 근거

ORD 기록
ord-8718fe05108841e99727674bbeb5add6
출처 데이터셋
uspto-grants-1979_01
특허 번호
US04136256

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