Dimethylformamide → HCID 20237791, compound

HRID 365207Notes

Reaction equation

HRID 365207 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:2]1[O:4][CH2:3]1.[NH2:12][CH2:13][CH2:14][NH:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][N:20]=[CH:19]2.CN(C)C=O.C(Cl)Cl.CO>O>[O:5]([CH2:1][CH:2]([OH:4])[CH2:3][NH:12][CH2:13][CH2:14][NH:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][N:20]=[CH:19]2)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 31217Phenyl glycidyl etherHCID 19354443HCID 19354443, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 20237791HCID 20237791, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.0 g. Phenyl glycidyl ether and 7.0 g. 5-(2-aminoethylamino)-indazole are dissolved in 10 ml. dimethylformamide by briefly heating to 70° C. and then left to stand for 24 hours at ambient temperature. The reaction mixture is shaken with 400 ml. methylene chloride-methanol (8:2 v/v) and 200 ml. water. The organic phase is evaporated and the residue obtained is purified by column chromatography on silica gel using, as elution agent, methylene chloride-methanol (9:1 v/v) and methylene chloride-ammonia-saturated methanol (9:1 v/v). The residue of the pure fractions is boiled under reflux for 1 hour with 50 ml. ethyl acetate and, after cooling, filtered off with suction and recrystallized from isopropyl alcohol, with the use of active charcoal. There are obtained 1.7 g. (26% of theory) of the desired product in the form of almost colorless crystals, which sinter at 137° C. and melt at 141°-144° C.

Workup

  1. waitleft
  2. customThe organic phase is evaporated
  3. customthe residue obtained
  4. customis purified by column chromatography on silica gel using, as elution agent, methylene chloride-methanol (9:1 v/v) and methylene chloride-ammonia-saturated methanol (9:1 v/v)
  5. temperatureunder reflux for 1 hour with 50 ml
  6. temperatureethyl acetate and, after cooling
  7. filtrationfiltered off with suction
  8. customrecrystallized from isopropyl alcohol, with the use of active charcoal
  9. customThere are obtained 1.7 g

Sources & evidence

ORD record
ord-c14027eb5edd404880689a8f65c7d2e3
Source dataset
uspto-grants-1986_08
Patent number
US04608383

Reaction notes

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