Cyanogen Bromide → HCID 68547517, compound

HRID 2359897Notes

Reaction equation

HRID 2359897 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:21]([O-])=O)=[C:6]([CH2:8][NH:9][CH2:10][C:11]2[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:12]=2[O:19][CH3:20])[CH:7]=1.[N:24]#[C:25]Br>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:21]=[C:25]([NH2:24])[N:9]([CH2:10][C:11]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:12]=1[O:19][CH3:20])[CH2:8]2

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 68551576HCID 68551576, compound

Product 1

HCID 68547517HCID 68547517, compoundYield 122.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

1-(5-Chloro-2-nitrophenyl)-N-(2,6-dimethoxybenzyl)methanamine (6.50 g, 21.2 mmol) was dissolved in 160 mL dioxane and cyanogen bromide (3.24 g, 29.6 mmol) dissolved in 20 mL dioxane was added. A slightly yellowish suspension was formed immediately. The reaction mixture was heated for 2 hours at reflux. The entire reaction mixture was completely dissolved at 85° C. and a colorless precipitate began to form at 75° C. The mixture was cooled to room temperature and stirring was continued for 12 hours. The resulting precipitate was filtered out and rewashed with dioxane (2×), isolating the crude product (8.6 g) after drying in a vacuum drying cabinet at 40° C. For purification and release of the hydrobromide salt, the solids were dissolved in dichloromethane again and alkalized with 2N sodium hydroxide solution. A portion of the product was precipitated immediately, filtered out and dried. The two phases of the mother liquor was separated and the resulting organic phase was washed with water (3×), whereupon a crystal product was again formed from it. The organic aqueous phase was concentrated in vacuo and the solids were filtered out. The two solids that were isolated in succession were combined.

Workup

  1. additionwas added
  2. customA slightly yellowish suspension was formed immediately
  3. temperatureThe reaction mixture was heated for 2 hours
  4. temperatureat reflux
  5. customThe entire reaction mixture
  6. dissolutionwas completely dissolved at 85° C.
  7. customto form at 75° C
  8. filtrationThe resulting precipitate was filtered out

Sources & evidence

ORD record
ord-5c248ce07d274303b9ea79bb03af09f1
Source dataset
uspto-grants-2014_04
Patent number
US08686002B2

Reaction notes

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