Hydrochloric Acid → HCID 20199179, compound

HRID 652088Notes

Reaction equation

HRID 652088 reaction equation
O1CC[O:3][CH:2]1[C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=1)[O:9][CH2:10][CH2:11][CH2:12][NH2:13].CS[C:19]([N:33]([CH3:42])[N:34]=CC1C=CC=CC=1)=[N:20][C:21](=O)[CH2:22][S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:25])=[O:24].Cl.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.CC(C)=O>[CH3:42][N:33]1[C:19]([NH:13][CH2:12][CH2:11][CH2:10][O:9][C:8]2[CH:7]=[C:6]([CH:16]=[CH:15][CH:14]=2)[CH:2]=[O:3])=[N:20][C:21]([CH2:22][S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:25])=[O:24])=[N:34]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 127974473-[3-(1,3-Dioxolan-2-yl)phenoxy]propanamineHCID 54365749methyl-1-methyl-2-(phenylmethylene)-N-[2-(phenylsulphonyl)acetyl]hydrazine carboximidothioate

Product 1

HCID 20199179HCID 20199179, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent

Procedure

A mixture of 3-[3-(1,3-dioxolan-2-yl)phenoxy]propanamine (2.3 g) and methyl-1-methyl-2-(phenylmethylene)-N-[2-(phenylsulphonyl)acetyl]hydrazine carboximidothioate (4.0 g) was heated at 60° under water pump vacuum for 3 h. The reaction mixture was dissolved in toluene (100 ml), 5N hydrochloric acid (100 ml) and acetone (50 ml) and stirred at room temperature for 18 h. The aqueous layer was basified to pH 9 with potassium carbonate and extracted with ethyl acetate. The organic extract was evaporated to give the title compound as an amber gum (3.0 g) T.l.c. Methanol; Rf 0.8.

Workup

  1. temperaturewas heated at 60° under water
  2. customfor 3 h
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. customwas evaporated

Sources & evidence

ORD record
ord-636c917019a2411982d19ecbd6fe0505
Source dataset
uspto-grants-1987_06
Patent number
US04670448

Reaction notes

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