Potassium Carbonate → HCID 20161923, compound

HRID 247167Notes

Reaction equation

HRID 247167 reaction equation
C([NH:9][C:10]([NH:12][CH2:13][CH2:14][S:15][CH2:16][C:17]1[O:18][C:19]([CH2:22][N:23]([CH3:25])[CH3:24])=[CH:20][CH:21]=1)=[S:11])(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[CH3:25][N:23]([CH2:22][C:19]1[O:18][C:17]([CH2:16][S:15][CH2:14][CH2:13][NH:12][C:10]([NH2:9])=[S:11])=[CH:21][CH:20]=1)[CH3:24]

Participants

5

Reactant 2

HCID 11430Potassium Carbonate2×HCID 20161927HCID 20161927, compound

Product 1

HCID 20161923HCID 20161923, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 24.76 g (65.6 mmol) of N-benzoyl-N'-(2-(((5-(dimethylamino)methyl-2-furanyl)methyl)thio)ethyl)-thiourea and 5.6 g (40.5 mmol) of potassium carbonate in 160 ml ethanol and 100 ml water is heated under stirring at 65° C. An additional amount of 3.45 g (25 mmol) potassium carbonate is added after 30 and 75 minutes respectively. After 90 minutes the ethanol is eliminated by vacuum distillation. A reaction mixture is diluted with 200 ml 5% sodium carbonate and extracted with dichloromethane (3×250 ml). The organic compound is washed with 5% sodium carbonate (2×500 ml), dried over anhydrous magnesium sulfate and concentrated to a brown oil. After chromatography on 500 g silica gel in dichloromethane/methanol 9:1, 16.8 g of N-(2-(((5-(dimethylamino)methyl-2-furanyl)methyl)thio)ethyl-thiourea oil is obtained.

Workup

  1. temperatureis heated
  2. distillationAfter 90 minutes the ethanol is eliminated by vacuum distillation
  3. additionA reaction mixture is diluted with 200 ml 5% sodium carbonate
  4. extractionextracted with dichloromethane (3×250 ml)
  5. washThe organic compound is washed with 5% sodium carbonate (2×500 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated to a brown oil

Sources & evidence

ORD record
ord-81ba8e680d524eeab41b48dfe06b679a
Source dataset
uspto-grants-1987_11
Patent number
US04705873

Reaction notes

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