Ethanolamine → benzyl N-(2-hydroxyethyl)carbamate

HRID 1955299Notes

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

Conditions

Temperature: 10 °C

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 (129 L). 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 (83 L) was added, the layers separated, and the aqueous layer extracted again with 83 L of ethyl acetate. The combined organic extracts were concentrated under vacuum to a volume of 38 L, 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.),7.37-7.1 (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

stirringto stir at room temperature overnight
customthe layers separated
extractionthe aqueous layer extracted again with 83 L of ethyl acetate
concentrationThe combined organic extracts were concentrated under vacuum to a volume of 38 L
stirringThe resulting slurry was stirred
filtrationfiltered
washThe solids were washed with isopropyl ether and vacuum
customdried

Sources & evidence

ORD record: ord-3fc6996a6eda414e9cc6a99dd5346e5f
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06124457

Reaction notes

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