Benzene → HCID 21505854, compound

HRID 1287659Notes

Reaction equation

HRID 1287659 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[CH2:6]([N:8](CC)[CH2:9][CH3:10])C.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(Cl)Cl)=[CH:16][CH:15]=1.C1C=CC=CC=1.C(#[N:37])C>>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:20]([C:6]1[NH:8][CH:9]=[CH:10][N:37]=1)([C:17]1[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 5

HCID 241BenzeneHCID 795ImidazoleHCID 6342AcetonitrileHCID 8471TriethylamineHCID 11000180HCID 11000180, compound

Product 1

HCID 21505854HCID 21505854, compound

Conditions

Temperature
80 °C

Procedure

To a solution of 27.2 g (0.4 mol) imidazole and 40.4 g (0.4 mol) triethylamine in 300 ml acetonitrile there are added dropwise 54 g (0.2 mol) 4-chlorophenyl-phenyl-dichloromethane. The triethylamine hydrochloride formed starts to separate at room temperature. The mixture is heated at 80° C for 12 hours to complete the reaction. After cooling, the reaction mixture is stirred with 500 ml benzene and washed with water until free of salt. The benzene solution is dried over anhydrous sodium sulphate, filtered and concentrated by evaporation; after recrystallisation of the crude product from acetonitrile, there result 41 g of pure bis-imidazolyl-4-chlorophenyl-phenylmethane of m.p. 140° C.

Workup

  1. customThe triethylamine hydrochloride formed starts to separate at room temperature
  2. customthe reaction
  3. temperatureAfter cooling
  4. washwashed with water until free of salt
  5. dry with materialThe benzene solution is dried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation
  8. customafter recrystallisation of the crude product from acetonitrile, there

Sources & evidence

ORD record
ord-cc236cc539844003b39e608da311d303
Source dataset
uspto-grants-1976_10
Patent number
US03985766

Reaction notes

Loading…