O-Xylene → Oxadixyl

HRID 1903405Notes

Reaction equation

HRID 1903405 reaction equation
[CH3:1][O:2][CH2:3][C:4]([N:6]([C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:21])[NH:7][C:8]([O:10][CH2:11][CH2:12]Cl)=[O:9])=[O:5].C1(C)C(C)=CC=CC=1.[OH-].[Na+]>O>[CH3:1][O:2][CH2:3][C:4]([N:6]([C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:21])[N:7]1[CH2:12][CH2:11][O:10][C:8]1=[O:9])=[O:5]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 14798Sodium HydroxideHCID 204544942-Chloroethyl 2-(methoxyacetyl)-2-(2,6-dimethylphenyl)-hydrazinecarboxylate

Product 1

HCID 53735Oxadixyl

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

236.1 g (0.75 mol) 2-Chloroethyl 2-(methoxyacetyl)-2-(2,6-dimethylphenyl)-hydrazinecarboxylate, 375 ml xylene and 187 ml water are stirred with external cooling, while 82.5 ml (0.82 mol) of an aqueous solution of sodium hydroxide (containing ~0.4 g NaOH per ml) are added at a rate to maintain the internal temperature at approx. 20°. The mixture is stirred after completion of the addition for 1 hour at 20°, and for 2 hours at 0°. The solid is filtered off, washed with 150 ml water and dried to yield the title compound as a slightly coloured solid, m.p. 102°-103°.

Workup

  1. additionare added at a rate
  2. temperatureto maintain the internal temperature at approx. 20°
  3. additionafter completion of the addition for 1 hour at 20°
  4. filtrationThe solid is filtered off
  5. washwashed with 150 ml water
  6. customdried

Sources & evidence

ORD record
ord-3a043e315a854f77a75f624e2032c250
Source dataset
uspto-grants-1984_03
Patent number
US04436744

Reaction notes

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