Sodium hydride → HCID 178510938, compound

HRID 1278472Notes

Reaction equation

HRID 1278472 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9]#[N:10])=[CH:4][CH:3]=1.[H-].[Na+].Cl.Cl[CH2:21][C:22]1[N:23]=[CH:24][NH:25][CH:26]=1>>[NH:25]1[CH:26]=[C:22]([CH2:21][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:9]#[N:10])[N:23]=[CH:24]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 2298202-(4-fluorophenyl)-2-phenylacetonitrileHCID 178478565HCID 178478565, compound

Product 1

HCID 178510938HCID 178510938, compound

Conditions

Temperature
60 °C

Procedure

As described in Example 1, 3.0 g. of 2-(4-fluorophenyl)-2-phenylacetonitrile, 1.36 g. of 50% sodium hydride and 2.17 g. of 4-chloromethylimidazole hydrochloride were mixed, and the reaction mixture was stirred at 60° C. for 3 hours and then at ambient temperature for 65 hours. The reaction mixture was then worked up as described in Example 1 to obtain 2.60 g. of the free base of the product named above, which was identified by 60 mHz nuclear magnetic resonance analysis in CDCl3 : δ10.65 (broad m, 1H); 7.37 (m, 8H); 6.88 (d, 2H, J=9 Hz); 6.65 (s, 1H), 3.70 (s, 2H).

Workup

  1. waitat ambient temperature for 65 hours
  2. customto obtain 2.60 g

Sources & evidence

ORD record
ord-011e967adc974772bdb32f218f4f6925
Source dataset
uspto-grants-1981_07
Patent number
US04281141

Reaction notes

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