Hydrochloric Acid → HCID 18349741, compound

HRID 2268247Notes

Reaction equation

HRID 2268247 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:12]=[C:13]([C:18]([NH:21][CH2:22][CH2:23][CH2:24][N:25]2[CH:29]=[CH:28][N:27]=[CH:26]2)([CH3:20])[CH3:19])[CH:14]=[CH:15][C:16]=1[Cl:17].Cl>ClCCl.C(N(CC)CC)C>[Cl:17][C:16]1[CH:15]=[CH:14][C:13]([C:18]([NH:21][CH2:22][CH2:23][CH2:24][N:25]2[CH:29]=[CH:28][N:27]=[CH:26]2)([CH3:19])[CH3:20])=[CH:12][C:11]=1[NH:10][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 18349701HCID 18349701, compound

Product 1

HCID 18349741HCID 18349741, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

Benzoyl chloride (0.21 ml) was added to a solution of N-[1-(3-amino-4-chlorophenyl)-1-methylethyl]-3-(imidazol-1-yl)propylamine (0.50 g) in dichloromethane (50 ml) and triethylamine (0.25 ml) with stirring at 0° C. The mixture was allowed to warm up to ambient temperature and stirred at this temperature for 18 hours. The mixture was washed with water, dried and evaporated. The residue was purified by flash column chromatography on silica using ethyl acetate/methanol/triethylamine (8:1:1) as the mobile phase. The product was obtained as an oil which was added to ethereal hydrogen chloride to produce a gum. The gum was triturated and then left standing for 18 hours. The resulting solid was ground up, filtered and dried to give 2′-chloro-5′-{1-[3-(imidazol-1-yl)propylamino]-1-methylethyl}benzanilide.

Workup

  1. temperatureto warm up to ambient temperature
  2. stirringstirred at this temperature for 18 hours
  3. washThe mixture was washed with water
  4. customdried
  5. customevaporated
  6. customThe residue was purified by flash column chromatography on silica
  7. customThe product was obtained as an oil which
  8. customto produce a gum
  9. customThe gum was triturated
  10. waitleft
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-ca11b6cace0d403ebbdedd5f56677769
Source dataset
uspto-grants-2001_12
Patent number
US06326500B1

Reaction notes

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