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

HRID 467086

Reaction equation

HRID 467086 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-0c7cdef324e84958856a1348304f2bf5
Source dataset
uspto-grants-1992_10
Patent number
US05158964

Linked notes

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