Sodium borohydride → HCID 20329861, compound

HRID 2058085Notes

Reaction equation

HRID 2058085 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]=[CH:9][C:10]2[CH:24]=[CH:23][C:13]([O:14][C:15]([CH3:22])([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+]>CO>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:14][C:15]([CH3:21])([CH3:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20329878HCID 20329878, compound

Product 1

HCID 20329861HCID 20329861, compoundYield 135%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 40 ml of methanol is dissolved 4.0 g of ethyl 2-[4-{N-(3-chlorophenyl)formimidoyl}phenoxy]-2-methylpropionate. Over a period of 1 hour, 0.44 g of sodium borohydride is added to the solution at 15° to 20° C. with cooling and stirring, and the mixture is stirred at the same temperature for 1 hour. After the reaction, the methanol is distilled off, and the residue is dissolved in ether. The solution is washed with water and dried. After drying, the ether is distilled off, and the resulting oily residue (3.8 g) is dissolved in 30 ml of ether. A mixture of hydrochloric acid and ethanol is added to the solution, and the resulting mixture is left to stand. The precipitated crystals are filtered off and washed with ether to give 3.0 g of ethyl 2-[4-(3-chloroanilinomethyl)phenoxy]-2-methylpropionate hydrochloride, mp 138° to 142° C. Recrystallization of the crystals from a mixture of ethanol and ether gives 1.6 g of crystals, mp 146° to 148° C.

Workup

  1. temperaturewith cooling
  2. stirringthe mixture is stirred at the same temperature for 1 hour
  3. customAfter the reaction
  4. distillationthe methanol is distilled off
  5. dissolutionthe residue is dissolved in ether
  6. washThe solution is washed with water
  7. customdried
  8. customAfter drying
  9. distillationthe ether is distilled off
  10. dissolutionthe resulting oily residue (3.8 g) is dissolved in 30 ml of ether
  11. additionA mixture of hydrochloric acid and ethanol
  12. additionis added to the solution
  13. waitthe resulting mixture is left
  14. filtrationThe precipitated crystals are filtered off
  15. washwashed with ether

Sources & evidence

ORD record
ord-d9bbeb30bebb4c669ab19f87eccab745
Source dataset
uspto-grants-1980_07
Patent number
US04214094

Reaction notes

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