Dimethylformamide → HCID 20368819, compound

HRID 616715Notes

Reaction equation

HRID 616715 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[CH2:19]C[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)C=O.[H-].[Na+].CI>C1C=CC=CC=1>[C:1]1([C:7]2[NH:8][C:9]3[CH2:19][C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[C:10]=3[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20368779HCID 20368779, compound

Product 1

HCID 20368819HCID 20368819, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 2-phenyl-4,5-dihydro-naphtho[1,2-d]imidazole (2.46 g.) dissolved in 10 ml. of dimethylforamide, 0.5 g. of 55% NaH (mineral oil dispersion) and 1.41 g. of methyl iodide are added. After stirring for two hours at room temperature, and for one hour at 60° C., the mixture is poured into ice water. The resulting solid precipitate is dissolved in benzene and chromatographed through a silica gel column and eluted with benzene containing 10% of ethyl ether for separating the two methylated isomers. The first eluted isomer (1.66 g.) melts at 150° C. (from ethanol) while the second (0.79 g.) melts at 141°-3° C. By operating according to the procedure described in Example 1, utilizing as the starting material 2-bromo-1-indanone, 2-phenyl-1,8-dihydro-indeno[1,2-d]imidazole (m.p. 231-2) is obtained which is in turn methylated according to the procedure described above to give 1-methyl-2-phenyl-8H-indeno[1,2-d]-imidazole, 3-methyl-2-phenyl-8-indeno[1,2-d]imidazole.

Workup

  1. waitfor one hour at 60° C.
  2. customchromatographed through a silica gel column
  3. washeluted with benzene containing 10% of ethyl ether
  4. customfor separating the two methylated isomers

Sources & evidence

ORD record
ord-25487562f454492b8419271d301ea70c
Source dataset
uspto-grants-1978_02
Patent number
US04075342

Reaction notes

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