Acetonitrile → HCID 73676527, compound

HRID 2399012Notes

Reaction equation

HRID 2399012 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]1=[CH:17][C:18]([CH:20]=[C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]1[CH3:31])=O.[Cl:32]([O-:36])(=[O:35])(=[O:34])=[O:33].C([NH+]1C2=NC3C(N=C2N(CC)C1C#CC=C1N(CC)C2=NC4C(N=C2N1CC)=CC=CC=4)=CC=CC=3)C.C(#N)C>N1C=CC=CC=1>[Cl:32]([O-:36])(=[O:35])(=[O:34])=[O:33].[CH3:6][N+:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[C:17]#[C:18][CH:20]=[C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]1[CH3:31]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 24813Phosphorus oxychlorideHCID 54247884HCID 54247884, compoundHCID 86734772HCID 86734772, compound

Product 1

HCID 73676527HCID 73676527, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Phosphoryl chloride (1.0 ml) is added to a stirred suspension of 1,3-Bis(1-methyl-2-(1H)-quinolylidene)acetone (0.68 g, 0.002 mol) in pyridine (10 ml). The mixture is stirred for 5 min., then the solid is collected and washed with a little pyridine, then with ether. The dye is converted to its perchlorate salt by solution in methanol, followed by addition of aqueous sodium perchlorate solution. After recrystallization from acetonitrile, the yield of purified dye is 0.30 g (36%) with the melting point indistinct. The following two dyes were prepared by procedures similar to that described above: 1,3-Diethyl-2-[(1,3-diethyl-1H-imidazo[4,5-b]quinoxalin-2-(3H)-ylidene)-1-propynyl]-1H-imidazo[4,5-b]quinoxalinium perchlorate. ##STR20##Recrystallized from acetonitrile. Purified yield 35%. mp > 300°. 1,3,3-Trimethyl-2-[(1,3,3-trimethyl-2-indolinylidene)-1-propynyl]-3H-indolium perchlorate. ##STR21##Recrystallized from methanol. Purified yield 43% mp 194°-7° dec.

Workup

  1. customthe solid is collected
  2. washwashed with a little pyridine
  3. additionfollowed by addition of aqueous sodium perchlorate solution
  4. customAfter recrystallization from acetonitrile
  5. customThe following two dyes were prepared by procedures similar to
  6. customPurified yield 35%
  7. customPurified yield 43% mp 194°-7° dec.

Sources & evidence

ORD record
ord-3e9aad2977ce46b4b2e8cd1d780071d9
Source dataset
uspto-grants-1977_05
Patent number
US04026884

Reaction notes

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