2-Amino-4-Nitrophenol → 2-(Chloromethyl)-5-nitro-1,3-benzoxazole

HRID 345028

Reaction equation

HRID 345028 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].Cl.[Cl:13][CH2:14][C:15](=N)OCC>C(O)C>[Cl:13][CH2:14][C:15]1[O:11][C:3]2[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 36133892-Amino-4-NitrophenolHCID 12470659Ethyl 2-chloroethanecarboximidate hydrochloride

Product 1

HCID 27641892-(Chloromethyl)-5-nitro-1,3-benzoxazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Amino-4-nitrophenol (10 g, 65 mmole) and ethyl chloroacetimidate hydrochloride (15.4 g, 97.5 mmole) were heated at reflux temperature in ethanol (100 ml) for 18 hours. The solvent was then removed by evaporation in vacuo and the residue recrystallised from ethanol to give the title compound, yield 9.0 g, m.p. 216°-217°.

Workup

  1. customThe solvent was then removed by evaporation in vacuo
  2. customthe residue recrystallised from ethanol

Sources & evidence

ORD record
ord-a27496733853466f80a3f59eb0fe0137
Source dataset
uspto-grants-1991_10
Patent number
US05055473

Linked notes

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