Water → HCID 14552587, compound

HRID 2309836Notes

Reaction equation

HRID 2309836 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:18]=[CH:17][C:7]([O:8][CH2:9][CH2:10][NH:11][C:12](=[O:16])[O:13][CH2:14][CH3:15])=[CH:6][CH:5]=1.[CH3:19][CH:20](Br)[CH2:21][CH3:22].O>O1CCCC1.CN(C=O)C>[CH3:19][CH:20]([O:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][CH2:10][NH:11][C:12](=[O:16])[O:13][CH2:14][CH3:15])=[CH:17][CH:18]=1)[CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 962WaterHCID 65542-BromobutaneHCID 24758Sodium hydrideHCID 14552586Ethyl N-[2-(4-hydroxyphenoxy)ethyl]carbamate

Product 1

HCID 14552587HCID 14552587, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent3×

Procedure

To pre-washed sodium hydride (0.106 g, 4.4 mmol) in 5 ml of tetrahydrofuran (THF) and 5 ml of DMF at RT is added ethyl N-[2-(4-hydroxyphenoxy)ethyl]carbamate (1.0 g, 4.4 mmol) in 5 ml of THF. The mixture is stirred at RT for 1.5 hours and is then cooled to -5°. 1-Methylpropyl bromide (0.72 g, 5.3 mmol) in 2 ml of THF is added to the mixture, followed by addition of 5 ml of DMF. The reaction mixture is allowed to warm slowly to RT, and is then heated at 60° for 18 hours. The reaction is cooled to RT and poured into water, and the mixture is extracted with ether (3X). The combined ether layers are washed with water until neutral, followed with brine, and dried over calcium sulfate. The solvent is removed in vacuo and purification by prep. TLC yields ethyl N-{2-[4-(1-methylpropoxy)phenoxy]ethyl}carbamate.

Workup

  1. temperatureis then cooled to -5°
  2. temperatureto warm slowly to RT
  3. temperatureis then heated at 60° for 18 hours
  4. temperatureThe reaction is cooled to RT
  5. extractionthe mixture is extracted with ether (3X)
  6. washThe combined ether layers are washed with water until neutral,
  7. dry with materialdried over calcium sulfate
  8. customThe solvent is removed in vacuo and purification by prep

Sources & evidence

ORD record
ord-476fa84304834f2ab0f34bf57cc1ce3a
Source dataset
uspto-grants-1987_09
Patent number
US04697033

Reaction notes

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