Water → HCID 20566525, compound

HRID 848219Notes

Reaction equation

HRID 848219 reaction equation
[OH:1][C:2]([CH3:12])([CH:6]([CH3:11])[CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][CH2:4][NH2:5].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21].O>CCO>[OH:1][C:2]([CH3:12])([CH:6]([CH3:11])[CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][CH2:4][NH:5][C:20](=[O:21])[O:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 10928Ethyl chloroformateHCID 20566535HCID 20566535, compound

Product 1

HCID 20566525HCID 20566525, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred suspension of 3-hydroxy-3,4-dimethyoctylamine (4.91 g; 28.38 mmole) and anhydrous sodium carbonate (5 g) in dry etanol (40 ml) was added ethyl chloroformate (3.65 g; 33.6 mmole) in dry ethanol (25 ml), over 30 min. The mixture was heated under reflux for 1 hr and then poured into water (200 ml). The product was extracted into diethyl ether (3×100 ml), and the combined organic layers washed with dilute hydrochloric acid (1×100 ml) and brine (1×100 ml) and dried. (Na2SO4). Evaporation in vacuo gave ethyl N-[3-hydroxy-3,4-dimethyloctyl]-carbamate (6.2 g; 891).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. extractionThe product was extracted into diethyl ether (3×100 ml)
  4. washthe combined organic layers washed with dilute hydrochloric acid (1×100 ml) and brine (1×100 ml)
  5. customdried
  6. customEvaporation in vacuo

Sources & evidence

ORD record
ord-bcf083b948a34c09861b5529754dfe93
Source dataset
uspto-grants-1981_10
Patent number
US04294972

Reaction notes

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