Water → benzyl N-[3-(1,2-dihydroxyethyl)phenyl]carbamate

HRID 221404Notes

Reaction equation

HRID 221404 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:11])[CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.O.C([O-])([O-])=O.[Na+].[Na+].[CH2:19]([O:26][C:27](Cl)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[OH:11][CH:8]([C:4]1[CH:3]=[C:2]([NH:1][C:27](=[O:28])[O:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:7]=[CH:6][CH:5]=1)[CH2:9][OH:10]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 149970331-(3-Aminophenyl)ethane-1,2-diol

Product 1

HCID 67328809benzyl N-[3-(1,2-dihydroxyethyl)phenyl]carbamateYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-(3-Aminophenyl)ethane-1,2-diol (10 g) was dissolved in DCM (80 mL). H2O (80 mL) and Na2CO3 (10.98 g) were added and the mixture cooled to 0° C. Benzylchloroformate (22 g) was added drop-wise over 20 minutes and the reaction mixture stirred at room temperature overnight. The organic phase was separated, dried over Na2SO4 and concentrated to give a crude product which was purified by column chromatography to give the title compound (8 g, 45%).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto give a crude product which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-b62b1556e9d5430fb1e36236a01923d9
Source dataset
uspto-grants-2012_06
Patent number
US08207167B2

Reaction notes

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