Hydrochloric Acid → Ethyl N-[2-(4-hydroxyphenyl)ethyl]carbamate

HRID 601572노트

반응식

HRID 601572 반응식
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[NH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.[OH-].[Na+].Cl>O1CCCC1.O>[CH2:5]([O:4][C:2](=[O:3])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[CH3:6]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 5610TyramineHCID 10928Ethyl chloroformateHCID 14798Sodium Hydroxide

생성물 1

HCID 2762412Ethyl N-[2-(4-hydroxyphenyl)ethyl]carbamate수율 84.9%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Add dropwise via an addition funnel a solution of ethyl chloroformate (0.74 mL, 7.7 mmol) in tetrahydrofuran (7 mL) to a stirred solution of tyramine (1.0 g, 7.3 mmol), sodium hydroxide (0.7 g, 17.1 mmol), and water (7 mL). Stir at room temperature for 18 hours then pour the reaction into 1N aqueous hydrochloric acid so the pH=1-2. Extract with ethyl acetate (3×25 mL). Dry the combined ethyl acetate extracts over sodium chloride/magnesium sulfate, filter, and concentrate on a rotary evaporator to yield 1.3 g, 6.2 mmol of [2-(4-hydroxy-phenyl)-ethyl]-carbamic acid ethyl ester: 1H NMR (CDCl3, 300.00 MHz): 7.01 (d, 2H); 6.78 (d, 2H); 6.26 (s, 1H); 4.78 (s, 1H); 4.14-4.09 (m, 2H); 3.40-3.38 (m, 2H); 2.74-2.69 (m, 2H); 1.24-1.19 (m, 3H).

후처리

  1. additionthen pour
  2. extractionExtract with ethyl acetate (3×25 mL)
  3. dry with materialDry the combined ethyl acetate
  4. filtrationfilter
  5. concentrationconcentrate on a rotary evaporator

출처 및 근거

ORD 기록
ord-2a8a5e853188419d9ddba97f6734b95f
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902372B2

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