2-[(2-Chloro-5-methylphenoxy)methyl]oxirane → HCID 19853091, compound

HRID 1607128Notes

Reaction equation

HRID 1607128 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:3]=1[O:4][CH2:5][CH:6]1[O:8][CH2:7]1.[O:14]([CH2:18][CH2:19][CH2:20][NH:21][C:22]([NH:24][CH2:25][CH2:26][NH2:27])=[O:23])[N+:15]([O-:17])=[O:16]>C(O)CCC>[Cl:1][C:2]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:3]=1[O:4][CH2:5][CH:6]([OH:8])[CH2:7][NH:27][CH2:26][CH2:25][NH:24][C:22]([NH:21][CH2:20][CH2:19][CH2:18][O:14][N+:15]([O-:17])=[O:16])=[O:23]

Participants

4

Reactant 2

HCID 130128362-[(2-Chloro-5-methylphenoxy)methyl]oxiraneHCID 19853032HCID 19853032, compound

Product 1

HCID 19853091HCID 19853091, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

3.1 g. 1-(2-Chloro-5-methylphenoxy)-2,3-epoxypropane and 8.5 g. 2-[(3-nitroxypropylamino)-carbonylamino]-ethylamine in 100 ml. n-butanol are stirred at ambient temperature for 18 hours. The solvent is distilled off at 30° C. bath temperature under oil pump vacuum, the residue is dissolved in 150 ml. ethyl acetate and this solution is washed 4 times with 60 ml. amounts of water. The organic phase is dried and evaporated and the residue is chromatographed on silica gel with methylene chloride/methanol (6:4 v/v). The appropriate fractions are evaporated and the residue is triturated with diethyl ether, filtered off with suction and dried. There are obtained 2.2 g. (35% of theory) of the desired product in the form of crystals; m.p. 109°-111° C.

Workup

  1. distillationThe solvent is distilled off at 30° C. bath temperature under oil pump vacuum
  2. dissolutionthe residue is dissolved in 150 ml
  3. washethyl acetate and this solution is washed 4 times with 60 ml
  4. customThe organic phase is dried
  5. customevaporated
  6. customthe residue is chromatographed on silica gel with methylene chloride/methanol (6:4 v/v)
  7. customThe appropriate fractions are evaporated
  8. customthe residue is triturated with diethyl ether
  9. filtrationfiltered off with suction
  10. customdried
  11. customThere are obtained 2.2 g

Sources & evidence

ORD record
ord-e1bea057c22d4b57b1a2eec6db82c3c6
Source dataset
uspto-grants-1989_09
Patent number
US04863949

Reaction notes

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