Sodium hydride → HCID 178510935, compound

HRID 1278470Notes

Reaction equation

HRID 1278470 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:11]#[N:12])=[CH:6][CH:5]=1.Cl.Cl[CH2:21][C:22]1[N:23]=[CH:24][NH:25][CH:26]=1>CN(C)C=O>[NH:25]1[CH:26]=[C:22]([CH2:21][C:10]([C:7]2[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=2)([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:11]#[N:12])[N:23]=[CH:24]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 4414244(4-Chlorophenyl)phenylacetonitrileHCID 178478565HCID 178478565, compound

Product 1

HCID 178510935HCID 178510935, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

As described in Example 1, 2.04 g. of 50% sodium hydride, 10.12 g. of 2-(4-chlorophenyl)-2-phenylacetonitrile, and 3.06 g. of 4-chloromethylimidazole hydrochloride were reacted in 50 ml. of dimethylformamide. The reaction mixture was stirred for one hour at 60° C. and then for 20 hours at ambient temperature. Evaporation of the solvent and work up as described in Example 1 produced 5.3 g. of the product named above, which was converted to the maleate salt and crystallized from acetone/diethyl ether to obtain 6.29 g. of the maleate salt of the desired product, m.p. 135°-136° C.

Workup

  1. waitfor 20 hours at ambient temperature
  2. customEvaporation of the solvent
  3. customproduced 5.3 g
  4. customcrystallized from acetone/diethyl ether
  5. customto obtain 6.29 g

Sources & evidence

ORD record
ord-e1c8a855b2c3480eb59c38d4b7d75d57
Source dataset
uspto-grants-1981_07
Patent number
US04281141

Reaction notes

Loading…