2-[(4-Methyl-2,3-dinitrophenoxy)methyl]oxirane → 4-{2-Hydroxy-3-[2-(2-methoxyphenoxy)-propylamino]-propoxy}-7-methyl-2-benzimidazolinone hydrochloride

HRID 67643Notes

Reaction equation

HRID 67643 reaction equation
[N+](C1C([N+]([O-])=O)=C(C)C=C[C:5]=1[O:14]CC1OC1)([O-])=O.C(NCC(OC1C=CC=CC=1OC)C)C1C=CC=CC=1.[ClH:39].Cl.Cl.[NH2:42][C:43]1[C:48]([NH2:49])=[C:47]([CH3:50])[CH:46]=[CH:45][C:44]=1[O:51][CH2:52][CH:53]([OH:68])[CH2:54][NH:55][CH2:56][CH:57]([O:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=1[O:66][CH3:67])[CH3:58]>C(O)C.[Pd]>[ClH:39].[OH:68][CH:53]([CH2:54][NH:55][CH2:56][CH:57]([O:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=1[O:66][CH3:67])[CH3:58])[CH2:52][O:51][C:44]1[C:43]2[NH:42][C:5](=[O:14])[NH:49][C:48]=2[C:47]([CH3:50])=[CH:46][CH:45]=1

Participants

6

Reactant 3

HCID 129266502-[(4-Methyl-2,3-dinitrophenoxy)methyl]oxiraneHCID 20527511HCID 20527511, compoundHCID 20527545HCID 20527545, compound

Product 1

HCID 205275354-{2-Hydroxy-3-[2-(2-methoxyphenoxy)-propylamino]-propoxy}-7-methyl-2-benzimidazolinone hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

30.5 g. 2,3-Dinitro-1-(2,3-epoxypropoxy)-4-methylbenzene and 32.6 g. N-benzyl-2-(2-methoxyphenoxy)-propylamine are boiled under reflux for 3 hours in 500 ml. ethanol. The reaction mixture is then hydrogenated in the presence of 10 g. 10% palladium-charcoal in 1 liter ethanol at 50° C. and 30 bar. The catalyst is filtered off and the filtrate is acidified with 2 N hydrochloric acid, clarified with active charcoal and evaporated to dryness. There are obtained 59 g. 2,3-diamino-1-{2-hydroxy-3-[2-(2-methoxyphenoxy)-propylamino]-propoxy}-4-methylbenzene trihydrochloride.

Workup

  1. temperatureunder reflux for 3 hours in 500 ml
  2. customat 50° C.
  3. filtrationThe catalyst is filtered off
  4. customevaporated to dryness
  5. customThere are obtained 59 g

Sources & evidence

ORD record
ord-c8258eaa93fa4aacabe0f63dfe4ea97d
Source dataset
uspto-grants-1982_08
Patent number
US04346093

Reaction notes

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