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

HRID 2224685Notes

Reaction equation

HRID 2224685 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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). Step 2 {2-[4-(4-Cyano-phenoxy)-phenyl]-ethyl}-carbamic acid ethyl ester

Workup

  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

Sources & evidence

ORD record
ord-c8e402e4c6014148ab4dbc7f9e841d68
Source dataset
uspto-grants-2008_05
Patent number
US07378448B2

Reaction notes

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