Benzoyl chloride → 2-(N-benzyloxycarbonylamino)-5-(N-benzylcarbonylamino)phenol

HRID 1885497Notes

Reaction equation

HRID 1885497 reaction equation
[C:1](Cl)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:12]=[CH:13][C:14]([NH:18][C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])=[C:15]([OH:17])[CH:16]=1.[C:29](=O)([O-])[O-:30].[Ca+2]>O1CCOCC1>[CH2:22]([O:21][C:19]([NH:18][C:14]1[CH:13]=[CH:12][C:11]([NH:10][C:29]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:30])=[CH:16][C:15]=1[OH:17])=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 10112Calcium CarbonateHCID 147457335-Amino-2-(benzyloxycarbonylamino)phenol

Product 1

HCID 147457402-(N-benzyloxycarbonylamino)-5-(N-benzylcarbonylamino)phenol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

12 g of benzoyl chloride are slowly added dropwise to 0.77 mole (20 g) of 5-amino-2-(benzyloxycarbonylamino)phenol (prepared in the 2nd stage of Example 1) and 12 g of calcium carbonate in 120 ml of dioxane brought to 80° C. The mixture is heated for a further 20 minutes after the addition is complete. The mixture is filtered while hot in order to remove the inorganic salts. The expected product is precipitated by diluting the filtrate with ice-cold water. When recrystallized from methoxyethanol, it melts at 252° C.

Workup

  1. custombrought to 80° C
  2. temperatureThe mixture is heated for a further 20 minutes
  3. additionafter the addition
  4. filtrationThe mixture is filtered while hot in order
  5. customto remove the inorganic salts
  6. customThe expected product is precipitated
  7. additionby diluting the filtrate with ice-cold water
  8. customWhen recrystallized from methoxyethanol, it melts at 252° C.

Sources & evidence

ORD record
ord-b37f28bf79554056bc20012edc1a7fa2
Source dataset
uspto-grants-1992_09
Patent number
US05145483

Reaction notes

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