N-bromobutanimide → HCID 10608244, compound

HRID 2259824Notes

Reaction equation

HRID 2259824 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].BrN1C(=O)CCC1=O.[N:21]#[C:22][NH2:23].[Na]>CN(C)C=O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11](=[N:23][C:22]#[N:21])[O-:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 67184N-bromobutanimide2×HCID 19001763N-(4-Nitrosophenyl)acetamideHCID 57375518Cyanamidnatrium

Product 1

HCID 10608244HCID 10608244, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(N-acetylamino)nitrosobenzene (15.0 g, 91.5 mmol) and N-bromosuccinimide (16.3, 91.6 mmol) were dissolved in dimethylformamide (150 ml). At ambient temperature, the solution was treated with monosodium cyanamide (9.14 g, 142.8 mmol). After 45 minutes, the brown solution was treated with N-bromosuccinimide (6.4 g, 36 mmol) and stirred for an additional 11/2 hours. The mixture was poured on ice-water (500 ml) and left overnight. The yellow crystallised precipitate was collected and dried to give 16.8 g 4-(N-acetylamino)phenyl-ONN-azoxycyanide as a yellow powder, m.pt. 240°-242° C. (Yield: 90% of theoretical).

Workup

  1. additionThe mixture was poured on ice-water (500 ml)
  2. waitleft overnight
  3. customThe yellow crystallised precipitate was collected
  4. customdried

Sources & evidence

ORD record
ord-8267a62dfab243188bc2b73175b253c7
Source dataset
uspto-grants-1995_12
Patent number
US05475093

Reaction notes

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