Bromine → HCID 178519460, compound

HRID 1439515Notes

Reaction equation

HRID 1439515 reaction equation
[C:1]([C:9]1[C:18]([CH3:19])=[N+:17]([O-:20])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N+:10]=1[O-:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:22]Br>CO>[C:1]([C:9]1[C:18]([CH2:19][Br:22])=[N+:17]([O-:20])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N+:10]=1[O-:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 178428812Methanone, (3-methyl-1,4-dioxido-2-quinoxalinyl)phenyl-

Product 1

HCID 178519460HCID 178519460, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred suspension of 28 g. (0.10 mol.) of 2-benzoyl-3-methylquinoxaline 1,4-dioxide in 1,000 ml. of methanol was added 5.6 ml. (0.11 mol.) of bromine. The reaction mixture was refluxed for 2 hours and then an additional 5.6 ml. (0.11 mol.) of bromine was added. The mixture was refluxed for an additional 2 hours and then it was cooled to 25° C. The solid which had precipitated was collected by filtration, washed with methanol, and dried to affored 30.4 g. (85% yield) of 2-benzoyl-3-bromomethylquinoxaline 1,4-dioxide, m.p. 183°-185° C.

Workup

  1. additionTo a stirred suspension of 28 g
  2. temperatureThe reaction mixture was refluxed for 2 hours
  3. temperatureThe mixture was refluxed for an additional 2 hours
  4. customThe solid which had precipitated
  5. filtrationwas collected by filtration
  6. washwashed with methanol
  7. customdried to affored 30.4 g

Sources & evidence

ORD record
ord-0568a3dd632d4e23865470e76a10dec1
Source dataset
uspto-grants-1977_11
Patent number
US04060523

Reaction notes

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