Calcium Carbonate → 5-(Ethoxycarbonylamino)-2-(benzyloxycarbonylamino)phenol

HRID 1885495Notes

Reaction equation

HRID 1885495 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[NH2:7][C:8]1[CH:9]=[CH:10][C:11]([NH:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])=[C:12]([OH:14])[CH:13]=1.C(=O)([O-])[O-].[Ca+2]>O1CCOCC1>[CH2:5]([O:4][C:2]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([NH:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])=[C:12]([OH:14])[CH:13]=1)=[O:3])[CH3:6]

Participants

5

Reactant 3

HCID 10112Calcium CarbonateHCID 10928Ethyl chloroformateHCID 147457335-Amino-2-(benzyloxycarbonylamino)phenol

Product 1

HCID 147457375-(Ethoxycarbonylamino)-2-(benzyloxycarbonylamino)phenol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.14 mole (15.7 g) of ethyl chloroformate is slowly added dropwise to 0.13 mole (33 g) of 5-amino -2-(benzyloxycarbonylamino)phenol (prepared in Example 1, 2nd stage) and 7.1 g of calcium carbonate in 100 ml of dioxane brought to 80° C. The mixture is heated for a further 20 minutes after the addition is complete. The reaction mixture is filtered while hot in order to remove the inorganic salts. The expected product is precipitated by diluting the cooled filtrate with ice-cold water. When recrystallized from ethyl acetate, it melts at 190° C.

Workup

  1. custombrought to 80° C
  2. temperatureThe mixture is heated for a further 20 minutes
  3. additionafter the addition
  4. filtrationThe reaction mixture is filtered while hot in order
  5. customto remove the inorganic salts
  6. customThe expected product is precipitated
  7. additionby diluting the cooled filtrate with ice-cold water
  8. customWhen recrystallized from ethyl acetate, it melts at 190° C.

Sources & evidence

ORD record
ord-60c21051c95c458da80631cd1ff0e295
Source dataset
uspto-grants-1992_09
Patent number
US05145483

Reaction notes

Loading…