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Acetic Anhydride → 5-acetamido-2-(N-benzyloxycarbonylamino)phenol

HRID 1885494
Notes
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Reaction equation

HRID 1885494 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[CH:10]=[CH:11][C:12]([NH:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[C:13]([OH:15])[CH:14]=1>O1CCOCC1>[C:1]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([NH:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[C:13]([OH:15])[CH:14]=1)(=[O:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 147457335-Amino-2-(benzyloxycarbonylamino)phenol

Product 1

HCID 147457345-acetamido-2-(N-benzyloxycarbonylamino)phenol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

0.6 mole (57 ml) of acetic anhydride is added dropwise to a solution of 0.6 mole (172 g) of 5-amino-2-(benzyloxycarbonylamino)phenol in 465 ml of dioxane heated to 70° C. After the reaction medium is cooled, the expected product precipitates. When recrystallized in 96° ethanol, it melts at 205° C.

Workup

  1. temperatureAfter the reaction medium is cooled
  2. customthe expected product precipitates
  3. customWhen recrystallized in 96° ethanol, it melts at 205° C.

Sources & evidence

ORD record
ord-40b5c779409548e6a896d002da09348e
Source dataset
uspto-grants-1992_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05145483

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes