Diethyl Ether → N-Methyl-2-[[3-[3-(1-piperidinylmethyl)phenoxy]propyl]aminothioxomethyl]-hydrazine carboxamide

HRID 4609

Reaction equation

HRID 4609 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:20]=[CH:21][CH:22]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]([NH:18][NH2:19])=[S:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:23][N:24]=[C:25]=[O:26].CCOCC>C1COCC1>[CH3:23][NH:24][C:25]([NH:19][NH:18][C:16]([NH:15][CH2:14][CH2:13][CH2:12][O:11][C:10]1[CH:20]=[CH:21][CH:22]=[C:8]([CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:9]=1)=[S:17])=[O:26]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 12228Methyl IsocyanateHCID 13402923N-(3-{3-[(Piperidin-1-yl)methyl]phenoxy}propyl)hydrazinecarbothioamide

Product 1

HCID 13657336N-Methyl-2-[[3-[3-(1-piperidinylmethyl)phenoxy]propyl]aminothioxomethyl]-hydrazine carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.62 g (5 mmol) of N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]hydrazine carbothioamide are dissolved in 30 ml of THF, 0.40 g (6 mmol) of methylisocyanate are added and the reaction mixture is left to stand overnight at room temperature. Ether is added to complete the precipitation, and the precipitate is suction filtered, washed with ether and recrystallised from ethanol. The analytical values are summarized in Table I.

Workup

  1. waitthe reaction mixture is left
  2. customthe precipitation
  3. filtrationfiltered
  4. washwashed with ether
  5. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-fc8d952f1485405099b4c829a6ef36c1
Source dataset
uspto-grants-1988_02
Patent number
US04727081

Linked notes

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