Triethyl orthoacetate → 2-Methyl-6-nitro-1,3-benzoxazol-4-ol

HRID 647221Notes

Reaction equation

HRID 647221 reaction equation
[NH2:1][C:2]1[C:8]([OH:9])=[CH:7][C:6]([N+:10]([O-:12])=[O:11])=[CH:5][C:3]=1[OH:4].[C:13](OCC)(OCC)(OCC)[CH3:14]>C1(C)C=CC=CC=1.C1COCC1>[N+:10]([C:6]1[CH:5]=[C:3]([OH:4])[C:2]2[N:1]=[C:13]([CH3:14])[O:9][C:8]=2[CH:7]=1)([O-:12])=[O:11]

Participants

5

Reactant 2

HCID 66221Triethyl orthoacetateHCID 204858732-Amino-5-nitrobenzene-1,3-diol

Product 1

HCID 204858692-Methyl-6-nitro-1,3-benzoxazol-4-olYield 39.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the 2-amino-5-nitroresorcinol (2.9 g, 0.017 mole) in toluene (50 ml) and THF (5 ml) was added triethyl orthoacetate (4.1 g, 0.0255 mole). This mixture was heated to reflux for one hour. Upon cooling, the product crystallized out of solution and was collected and dried to yield a tan solid (1.3 g, 39.4 percent). TLC showed the product to be pure.

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux for one hour
  3. temperatureUpon cooling
  4. customthe product crystallized out of solution
  5. customwas collected
  6. customdried

Sources & evidence

ORD record
ord-96063322e09144ec92f8a70e1a7ff405
Source dataset
uspto-grants-1983_10
Patent number
US04407930

Reaction notes

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