Hydrochloric Acid → HCID 70578042, compound

HRID 2412338Notes

Reaction equation

HRID 2412338 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:18]=[CH:19][CH:20]=2)[O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][NH2:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[NH:22][C:23](SC)=[CH:24][N+:25]([O-:27])=[O:26].Cl.[CH2:31](O)C>O>[CH3:31][N:17]([CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][C:10]1[CH:18]=[CH:19][CH:20]=[C:8]([CH2:7][N:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH:9]=1)[C:23]([NH2:22])=[CH:24][N+:25]([O-:27])=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 1235491-Methylthio-1-methylamino-2-nitroethyleneHCID 13020537HCID 13020537, compound

Product 1

HCID 70578042HCID 70578042, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 2-[2-[3-(1-piperidinylmethyl) phenoxy]ethoxy]ethanamine (0.4 g) and N-methyl-1-methylthio-2-nitro-etheneamine (0.24 g) in water (20 ml) and ethanol (20 ml) was stirred at 50° for 5h. The solution was diluted with water (20 ml) acidified to pH 1 with dilute hydrochloric acid and washed with ethyl acetate (2×50 ml). The aqueous solution was basified to pH 9 with potassium carbonate and extracted with ethyl acetate (3×50 ml). Evaporation of these organic extracts gave a yellow oil which solidified when triturated with cyclohexane. The solid was recrystallised from ethyl acetate (10 ml) to give the title compound as a white powder (0.17 g) m.p. 125.5°-126.5° .

Workup

  1. washwashed with ethyl acetate (2×50 ml)
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. customEvaporation of these organic extracts
  4. customgave a yellow oil which
  5. customtriturated with cyclohexane
  6. customThe solid was recrystallised from ethyl acetate (10 ml)

Sources & evidence

ORD record
ord-dc7ba22897cb47cf90408021aa6e2ffb
Source dataset
uspto-grants-1985_01
Patent number
US04491586

Reaction notes

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