Diketene → HCID 19967135, compound

HRID 2081608Notes

Reaction equation

HRID 2081608 reaction equation
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[CH2:14]=[C:15]1[O:18][C:17](=[O:19])[CH2:16]1>ClCCCl>[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:17](=[O:19])[CH2:16][C:15](=[O:18])[CH3:14])=[CH:9][CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 12661DiketeneHCID 12653194-Imidazol-1-ylmethylphenylamine

Product 1

HCID 19967135HCID 19967135, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred solution of 10 parts of 4-[(1H-imidazol-1-yl)methyl]benzenamine in 180 parts of 1,2-dichloroethane were added dropwise 3.9 parts of 4-methylene-2-oxetanone. After stirring for 1/2 hour at room temperature, the precipitate was filtered off, washed with 1,2-dichloroethane and dried, yielding 9.8 parts (74.8%) of N-[4-(1H-imidazol-1-ylmethyl)phenyl]-3-oxobutanamide; mp. 175° C.(interm. 57). In a similar manner there were also prepared the intermediates listed in Table 4:

Workup

  1. filtrationthe precipitate was filtered off
  2. washwashed with 1,2-dichloroethane
  3. customdried

Sources & evidence

ORD record
ord-835ddd30e41e4bea8d00382c4672746f
Source dataset
uspto-grants-1993_02
Patent number
US05185346

Reaction notes

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