Dimethylformamide → HCID 14415981, compound

HRID 2274129Notes

Reaction equation

HRID 2274129 reaction equation
[CH:1]1[C:6]2[C:7]3[C:16]([C:17]4[C:22]([C:5]=2[CH:4]=[CH:3][CH:2]=1)=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:15][CH:14]=[C:13]1[C:8]=3[CH:9]=[CH:10][CH:11]=[CH:12]1.CN(C)C=O.[Br:28]N1C(=O)CCC1=O>O>[Br:28][C:14]1[CH:15]=[C:16]2[C:7](=[C:8]3[C:13]=1[CH:12]=[CH:11][CH:10]=[CH:9]3)[C:6]1[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=1[C:22]1[C:17]2=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 9140Benzo(g)chryseneHCID 67184N-bromobutanimide

Product 1

HCID 14415981HCID 14415981, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

5.21 g of benzo[g]chrysene and 50 mL of N,N-dimethylformamide were placed in a flask. 10 mL of N,N-dimethylformamide solution of 4.00 g of N-bromosuccinimide were added. The resulting solution was heated with stirring at 80° C. for 8 hours. After cooling to room temperature, the reaction solution was poured to 200 mL of water. Deposited solids were filtered off, and washed with water and methanol. The resulting solids were purified by silica gel column chromatography, whereby 5.87 g (yield 88%) of 10-bromobenzo[g]chrysene was obtained.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureAfter cooling to room temperature
  3. filtrationDeposited solids were filtered off
  4. washwashed with water and methanol
  5. customThe resulting solids were purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c8b84886f94c46568ac984a45a03d1dc
Source dataset
uspto-grants-2015_09
Patent number
US09126943B2

Reaction notes

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