Dimethylformamide → [4-amino-1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazol-5-yl]ethanone

HRID 981871Notes

Reaction equation

HRID 981871 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]1[NH:11][CH:12]=[N:13][C:14]#[N:15].CN(C)C=O.[K].[CH3:23][C:24]([OH:27])(C)[CH3:25].BrCC(=O)C>O>[NH2:15][C:14]1[N:13]=[CH:12][N:11]([CH:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:10][C:2]2([CH3:16])[CH3:1])[C:23]=1[C:24](=[O:27])[CH3:25]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11715BromoacetoneHCID 86639980Potassium tert-butoxideHCID 178422614N-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-N'-cyanoformamidine

Product 1

HCID 20068367[4-amino-1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazol-5-yl]ethanoneYield 23%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

316 Parts of N-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-N'-cyanoformamidine were suspended in 282 parts of N,N-dimethylformamide. To this suspension were added slowly 163 parts of 2-methyl-2-propanol potassium salt and after stirring at room temperature for 4 hours there were added dropwise 194 parts of bromopropanone. After 48 hours, the reaction mixture was poured into water and extracted with 1,1'-oxybisethane. The separated organic layers were evaporated and the residue was crystallized first from a mixture of 1,1'-oxybisethane and petroleum ether. The precipitate was filtered off and dried and then recrystallized from methylbenzene. The product was filtered off and dried, yielding 93 parts (23%) of [4-amino-1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazol-5-yl]ethanone; mp. 174°-175° C.

Workup

  1. waitAfter 48 hours
  2. extractionextracted with 1,1'-oxybisethane
  3. customThe separated organic layers were evaporated
  4. customthe residue was crystallized first from a mixture of 1,1'-oxybisethane and petroleum ether
  5. filtrationThe precipitate was filtered off
  6. customdried
  7. customrecrystallized from methylbenzene
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-6c348cddbc2d40aa8b9701f40dd2724a
Source dataset
uspto-grants-1991_02
Patent number
US04994103

Reaction notes

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