Hydrochloric Acid → HCID 54199411, compound

HRID 325698Notes

Reaction equation

HRID 325698 reaction equation
[N:1]1([CH2:6][C:7]2[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=2)[O:10][CH2:11][CH2:12][CH2:13][NH2:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.CS[C:20]([N:24]([CH3:33])[N:25]=CC1C=CC=CC=1)=[N:21][C:22]#[N:23].Cl>CC(C)=O>[CH3:33][N:24]1[C:20]([NH:14][CH2:13][CH2:12][CH2:11][O:10][C:9]2[CH:15]=[CH:16][CH:17]=[C:7]([CH2:6][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH:8]=2)=[N:21][C:22]([NH2:23])=[N:25]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 127974543-{3-[(Pyrrolidin-1-yl)methyl]phenoxy}propan-1-amineHCID 54323404methyl N-cyano-1-methyl-2-(phenylmethylene)-hydrazinecarboximidothioate

Product 1

HCID 54199411HCID 54199411, compoundYield 14.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-[3-[1-pyrrolidinylmethyl]phenoxy]propanamine (0.97 g) and N-cyano-1-methyl-2-(phenylmethylene)hydrazine carboximidothioic acid methyl ester (0.97 g) was heated at 70° for 8 hr under a reduced pressure of 20 mm of mercury. Acetone was added and the solution was treated with hydrochloric acid at room temperature for one hour, washed with ether, basified with sodium carbonate and extracted with ethyl acetate. Evaporation of the ethyl acetate extracts gave a thick oil which crystallised from ethyl acetate/light petroleum (b.p. 60-80") to give the title compound as a white solid (0.2 g). TLC; silica/methanol/0.88 ammonia 80:1) Rf 0.5, m.p. 95°-95.5°.

Workup

  1. temperaturewas heated at 70° for 8 hr under a reduced pressure of 20 mm of mercury
  2. washwashed with ether
  3. extractionextracted with ethyl acetate
  4. customEvaporation of the ethyl acetate
  5. customextracts gave a thick oil which
  6. customcrystallised from ethyl acetate/light petroleum (b.p. 60-80")

Sources & evidence

ORD record
ord-04f043fc72684c6eade945d51ce753f9
Source dataset
uspto-grants-1984_04
Patent number
US04442110

Reaction notes

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