Isopropylamine → HCID 22765392, compound

HRID 259491Notes

Reaction equation

HRID 259491 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([NH:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][CH:6]1[O:8][CH2:7]1.[CH:19]([NH2:22])([CH3:21])[CH3:20]>C(O)C>[Cl:1][C:2]1[CH:12]=[C:11]([NH:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][CH:6]([OH:8])[CH2:7][NH:22][CH:19]([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 22765390HCID 22765390, compound

Product 1

HCID 22765392HCID 22765392, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 40 g of 1-[o-chloro-p-(N',N'-dimethyl-ureido)-phenoxy]-2,3-epoxy-propane and 40 g of isopropylamine in 40 ml of ethanol is heated to boiling for 4 hours. Thereafter the mixture is concentrated by evaporation in vacuo and the residue is dissolved in 2 N hydrochloric acid. After extraction with ether, the hydrochloric acid layer is separated off and rendered alkaline by adding concentrated sodium hydroxide solution. The base which has separated out is extracted by shaking with methylene chloride. After evaporation of the solvent and after recrystallisation of the residue from ethyl acetate, the 1-[o-chloro-p-(N',N'-dimethylureido)-phenyoxy]-2-hydroxy-3-isopropylamino-propane of formula ##STR18## is obtained in crystals of melting point 130° C.

Workup

  1. concentrationThereafter the mixture is concentrated by evaporation in vacuo
  2. dissolutionthe residue is dissolved in 2 N hydrochloric acid
  3. extractionAfter extraction with ether
  4. customthe hydrochloric acid layer is separated off
  5. additionby adding concentrated sodium hydroxide solution
  6. customThe base which has separated out
  7. extractionis extracted
  8. customAfter evaporation of the solvent
  9. customafter recrystallisation of the residue from ethyl acetate

Sources & evidence

ORD record
ord-d30e3c47ad3047778061e22dfb668e95
Source dataset
uspto-grants-1977_07
Patent number
US04038313

Reaction notes

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