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Dimethylformamide → HCID 21951484, compound

HRID 1760353
Notes
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Reaction equation

HRID 1760353 reaction equation
[N+]([C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=1)[C:8]#[N:9])([O-])=O.[OH:14][C:15]1[CH:20]=[CH:19][C:18](O)=[CH:17][C:16]=1[P:22](=[O:35])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C[N:37]([CH3:40])C=O.[C:41](=[O:44])([O-])[O-].[K+].[K+]>O>[C:12]([C:6]1[CH:5]=[C:4]([CH:11]=[CH:10][C:7]=1[C:8]#[N:9])[O:14][C:15]1[CH:20]=[CH:19][C:18]([O:44][C:41]2[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([C:40]#[N:37])[CH:5]=2)=[CH:17][C:16]=1[P:22](=[O:35])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)#[N:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 974431,2-Benzenedicarbonitrile, 4-nitro-HCID 27834952,5-Dihydroxyphenyl(diphenyl)phosphine Oxide

Product 1

HCID 21951484HCID 21951484, compound

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

Into a 250 mL three neck round bottomed flask equipped with a mechanical stirrer, nitrogen gas inlet, and drying tube was place 4-nitrophthalonitrile (9.9 g, 0.0572 mol), 2,5-dihydroxyphenyldiphenylphosphine oxide (8.87 g, 0.0286 mol), and N,N-dimethylformamide (DMAc, 100 mL). The mixture was stirred for 15 minutes at room temperature and then pulverized anhydrous potassium carbonate (9.89 g, 0.0715 mol, 2.5 eq.) was added. The reaction mixture was stirred at room temperature for 24 hours. The reddish-brown reaction mixture was poured into ˜700 mL of stirred water and the resulting off-white precipitate was collected and washed with water. The solid was stirred in 100 mL of methanol for 10 minutes and was collected and dried for 2 hours in a vacuum oven at 100° C.

Workup

  1. customdrying tube
  2. additionwas added
  3. stirringThe reaction mixture was stirred at room temperature for 24 hours
  4. customthe resulting off-white precipitate was collected
  5. washwashed with water
  6. stirringThe solid was stirred in 100 mL of methanol for 10 minutes
  7. customwas collected
  8. customdried for 2 hours in a vacuum oven at 100° C.

Sources & evidence

ORD record
ord-1f82603bacff4c3fabeafc3e9611f181
Source dataset
uspto-grants-2005_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06841652B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes