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p,p'-DDCN → HCID 178510939, compound

HRID 1278469
Notes
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Reaction equation

HRID 1278469 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[C:9]#[N:10])=[CH:4][CH:3]=1.[H-].[Na+].Cl.Cl[CH2:22][C:23]1[N:24]=[CH:25][NH:26][CH:27]=1>CN(C)C=O>[NH:26]1[CH:27]=[C:23]([CH2:22][C:8]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]#[N:10])[N:24]=[CH:25]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8806p,p'-DDCNHCID 24758Sodium hydrideHCID 178478565HCID 178478565, compound

Product 1

HCID 178510939HCID 178510939, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

As described in Example 1, 7.26 g. of 2,2-bis(4-chlorophenyl)acetonitrile, 1.33 g. of 50% sodium hydride and 2.12 g. of 4-chloromethylimidazole hydrochloride were reacted in 50 ml. of dimethylformamide. The mixture was stirred for 2 hours at 60° C. and then 21 hours at ambient temperature. The solvent was then evaporated off under vacuum and the reaction mixture was worked up as described in Example 1 to obtain 5.2 g. of the free base named above, which was converted to the maleate salt and crystallized from acetone/diethyl ether to obtain 5.73 g. of the maleate salt of the product named above, m.p. 151.5°-153° C.

Workup

  1. custom21 hours
  2. customat ambient temperature
  3. customThe solvent was then evaporated off under vacuum
  4. customto obtain 5.2 g
  5. customcrystallized from acetone/diethyl ether
  6. customto obtain 5.73 g

Sources & evidence

ORD record
ord-37b27b6dc4ec4f3f94789648c81585dd
Source dataset
uspto-grants-1981_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04281141

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes