Ethanolamine → benzyl N-(2-hydroxyethyl)carbamate

HRID 431271Notes

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 (34 gal, 128.7 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 (22 gal, 83.3 L) was added, the layers separated, and the aqueous layer extracted again with ethyl acetate (22 gal., 83.3 L). The combined organic extracts were concentrated under vacuum to a volume of 10 gal (37.9 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), 7.37-7.16 (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

stirringto stir at room temperature overnight
customthe layers separated
extractionthe aqueous layer extracted again with ethyl acetate (22 gal., 83.3 L)
concentrationThe combined organic extracts were concentrated under vacuum to a volume of 10 gal (37.9 L)
stirringThe resulting slurry was stirred
filtrationfiltered
washThe solids were washed with isopropyl ether and vacuum
customdried

Sources & evidence

ORD record: ord-16cd9178df3743aabb26968b987ac05b
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06657063B1

Reaction notes

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