Sodium hydride → HCID 178510932, compound

HRID 1278465Notes

Reaction equation

HRID 1278465 reaction equation
[Br: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.C(O)(=O)/C=C\C(O)=O>CN(C)C=O>[NH:25]1[CH:26]=[C:22]([CH2:21][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br: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

6

Reactant 4

HCID 24758Sodium hydrideHCID 444266Maleic AcidHCID 13156968HCID 13156968, compoundHCID 178478565HCID 178478565, compound

Product 1

HCID 178510932HCID 178510932, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

A 10.0 g. portion of 2-(4-bromophenyl)-2-phenylacetonitrile was mixed with 1.76 g. of 50% sodium hydride in 20 ml. of dimethylformamide, and 2.81 g. of 4-chloromethylimidazole hydrochloride in 20 ml. of dimethylformamide was added. The reaction mixture was then stirred at 100° C. for 5 hours, and at ambient temperature for 16 hours. The reaction mixture was worked up as described in Example 1 to obtain 6.1 g. of the free base of the compound named in the heading above. The compound was converted to the maleate salt by contact with maleic acid, and the salt was crystallized from diethyl ether/acetone to obtain 7.80 g. of product, m.p. 121°-124° C.

Workup

  1. waitat ambient temperature for 16 hours
  2. customto obtain 6.1 g
  3. customthe salt was crystallized from diethyl ether/acetone
  4. customto obtain 7.80 g

Sources & evidence

ORD record
ord-983d7da85c3f47e2abe3fc9c4b503b11
Source dataset
uspto-grants-1981_07
Patent number
US04281141

Reaction notes

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