Ethanolamine → benzyl N-(2-hydroxyethyl)carbamate

HRID 611619Notes

Reaction equation

HRID 611619 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:12]([CH2:14][NH2:15])[OH:13].C([O-])(O)=O.[Na+].C(OCC)(=O)C>O>[CH2:1]([O:8][C:9]([NH:15][CH2:14][CH2:12][OH:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 280458benzyl N-(2-hydroxyethyl)carbamateYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Benzylchloroformate (44.95 kg, 263.5 mol, 1.0 eq.) was added over a 2 hour period at room temperature to a solution of ethanolamine (16.1 kg, 263.5 mol, 1.0 eq.) in water (34 gal). After stirring for 30 minutes, this was added to a cold (5-10° C.) solution of NaHCO3 (33.2 kg, 395.25 mol, 1.5 eq) in H2O (330 L) over a 30 min period and then allowed to stir at room temperature overnight. Ethyl acetate (22 gal) was added, the layers separated, and the aqueous layer extracted again with 22 gal. ethyl acetate. The combined organic extracts were concentrated under vacuum to a volume of 10 gal, and the remainder displaced with isopropyl ether. The resulting slurry was stirred and cooled to +10° C. for 2 hours, then filtered. The solids were washed with isopropyl ether and vacuum dried to give the title compound(39.1 kg, 71.1%). mp 61-63° C. NMR (300 MHz, d6 -DMSO): δ=7.50-7.37 (m, 5H), 7.37-7.16 (m, 1H), 5.05 (s, 2H), 4.70-4.63 (m, 1H), 3.46-3.37 (m, 2H), 3.13-3.03 (m, 2H).

Workup

  1. stirringto stir at room temperature overnight
  2. customthe layers separated
  3. extractionthe aqueous layer extracted again with 22 gal
  4. concentrationThe combined organic extracts were concentrated under vacuum to a volume of 10 gal
  5. stirringThe resulting slurry was stirred
  6. temperaturecooled to +10° C. for 2 hours
  7. filtrationfiltered
  8. washThe solids were washed with isopropyl ether and vacuum
  9. customdried

Sources & evidence

ORD record
ord-2de5e19e8e9647d495960c174f777dd0
Source dataset
uspto-grants-1999_12
Patent number
US06001856

Reaction notes

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