Acetonitrile → HCID 12374308, compound

HRID 1415099Notes

Reaction equation

HRID 1415099 reaction equation
[Br-:1].[C:2]([CH2:5][CH2:6][N+:7]1[C:11]2[CH:12]=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:14]=[CH:15][C:10]=2[O:9][C:8]=1[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=O)[CH3:3].C(#N)C>CCOCC>[Br-:1].[CH3:3][C:2]1[CH2:5][CH2:6][N+:7]2[C:11]3[CH:12]=[C:13]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:14]=[CH:15][C:10]=3[O:9][C:8]=2[C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 12374306HCID 12374306, compound

Product 1

HCID 12374308HCID 12374308, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
30 °C

Procedure

1,3-Dihydro-3-methyl-4-phenylpyrido[2,1-b]-5-phenylbenzoxazolium bromide is prepared by reacting 3-(2-acetylethyl)-2-benzyl-5-phenylbenzoxazolium bromide (5.0 g.) dissolved in 75 ml. of acetonitrile. The reaction mixture is stirred at about 30° C for about 124 hours, after which ether is added to the solution and the resultant precipitate is filtered, washed and dried to give 4.27 g. (93% yield) of 1,2-dihydro-3-methyl-4,8-diphenylpyrido[2,1-b]benzoxazolium bromide having a melting point of 269° C. This product is dissolved in 20 ml. of dimethyl sulfoxide and heated for a few minutes on a hot plate. Sodium perchlorate (0.6 g.) in 20 ml. of ethanol is added with stirring. Excess diethyl ether is added, precipitating an oil. Crystallization of the oily substance is induced from a chloroform-ether solution. Recrystallization from ethanol affords a 70% yield of product having a melting point of 252°-254° C.

Workup

  1. dissolutiondissolved in 75 ml
  2. filtrationthe resultant precipitate is filtered
  3. washwashed
  4. customdried
  5. customto give 4.27 g

Sources & evidence

ORD record
ord-a58cb2db9c554aa9b9e528504693e8eb
Source dataset
uspto-grants-1977_01
Patent number
US04003750

Reaction notes

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