Dimethylformamide → HCID 19791786, compound

HRID 928377Notes

Reaction equation

HRID 928377 reaction equation
BrC[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[N-:15]=[N+:16]=[N-:17].[Na+].[CH3:19]N(C=O)C>>[N:15]([CH2:19][C:14]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:6]1[CH:5]=[CH:4][CH:3]=[CH:8][CH:7]=1)=[N+:16]=[N-:17]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 2577161,1'-Biphenyl, 4-(bromomethyl)-

Product 1

HCID 19791786HCID 19791786, compound

Conditions

Temperature
90 °C

Procedure

A mixture of 4-(Bromomethyl)-biphenyl (200 mg, 0.6 mmol) and sodium azide (41 mg, 0.6 mmol) in 2 mL DMF was stirred at 90° C. for 1 h. The reaction mixture was concentrated in vacuo and the residue was treated with DCM and extracted with water. The organic layer was dried over MgSO4 and evaporated to give the title compound which was used in the next step without further purification. 1H-NMR (CDCl3, 400 MHz) 7.62-7.66 (m, 4H), 7.39-7.50 (m, 5H), 4.42 (s, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was treated with DCM
  3. extractionextracted with water
  4. dry with materialThe organic layer was dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-69d2ac2102834714867001bff49a279d
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

Loading…