Triethylamine → Methyl 4-[2-(4-bromobenzamido)ethoxy]benzoate

HRID 1762179노트

반응식

HRID 1762179 반응식
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.C(Cl)(=O)OCC.[NH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=1>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:24][CH2:25][CH2:26][O:27][C:28]2[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=2)=[O:7])=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 114644-Bromobenzoic acidHCID 14097616Methyl 4-(2-aminoethoxy)benzoate

생성물 1

HCID 14097618Methyl 4-[2-(4-bromobenzamido)ethoxy]benzoate수율 56.7%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

p-Bromobenzoic acid (6 g) and 3.35 g of triethylamine were dissolved in 80 ml of chloroform, the mixture was cooled at 0°-5° C. with stirring, and 3.26 g of ethyl chlorocarbonate was dropped thereinto. The mixture was stirred at the same temperature for 30 minutes, 5.86 g of methyl 4-(2-aminoethoxy)benzoate was added, and the mixture was stirred for 7 hours more. The reaction solution was washed with 10% hydrochloric acid, saturated potassium carbonate solution, and with water, dried with anhydrous magnesium sulphate, concentrated in vacuo, the residue was crystallised with n-hexane, and 8.5 g of crystals obtained were recrystallised from ethyl acetate to give 6.4 g of the product, m.p. 134°-136° C.

후처리

  1. temperaturethe mixture was cooled at 0°-5° C.
  2. stirringThe mixture was stirred at the same temperature for 30 minutes
  3. stirringthe mixture was stirred for 7 hours more
  4. washThe reaction solution was washed with 10% hydrochloric acid, saturated potassium carbonate solution
  5. dry with materialwith water, dried with anhydrous magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customthe residue was crystallised with n-hexane, and 8.5 g of crystals
  8. customobtained
  9. customwere recrystallised from ethyl acetate

출처 및 근거

ORD 기록
ord-d862fe292fbb498f8de8139483112ffd
출처 데이터셋
uspto-grants-1989_05
특허 번호
US04831055

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