Water → HCID 73796188, compound

HRID 1580191Notes

Reaction equation

HRID 1580191 reaction equation
[N:1]([O-:3])=[O:2].[Na+].Br[CH2:6][C:7](=[N:12][OH:13])[C:8]([CH3:11])([CH3:10])[CH3:9].O>CS(C)=O>[CH3:9][C:8]([CH3:11])([CH3:10])[C:7](=[N:12][OH:13])[CH2:6][N+:1]([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 23668193Sodium NitriteHCID 85441254HCID 85441254, compound

Product 1

HCID 73796188HCID 73796188, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 18.2 g (0.26 m) of sodium nitrite in 130 ml of dimethyl sulfoxide is added, in portions, 29.0 g (0.15 m) of 1-bromo-3,3-dimethyl-2-butanone oxime. A mild exotherm results and external cooling is used to keep the temperature below 27° C. Additional solvent is added to maintain stirrability. After 20 hours stirring, the mixture is poured onto ice and water to give a solid which is collected on a filter. The 10 g of solid, m. 115°-120° C, thus obtained is recrystallized from a hot benzene-petroleum ether mixture to give 7 g of white crystals, m. 124°-125° C.

Workup

  1. customA mild exotherm results
  2. temperatureexternal cooling
  3. customthe temperature below 27° C
  4. additionAdditional solvent is added
  5. temperatureto maintain stirrability
  6. customto give a solid which
  7. customis collected on a filter
  8. custom115°-120° C, thus obtained
  9. customis recrystallized from a hot benzene-petroleum ether mixture

Sources & evidence

ORD record
ord-426ae7c099ef44b1bee2614148058c5c
Source dataset
uspto-grants-1976_01
Patent number
US03932471

Reaction notes

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