Potassium Carbonate → HCID 153274983, compound

HRID 987594Notes

Reaction equation

HRID 987594 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][C:16]=1[CH:17]([CH3:19])[CH3:18])[C:8]([NH:10][C:11]([NH2:13])=[NH:12])=[O:9])(=[O:4])=[O:3].[C:20]([O-:23])([O-])=O.[K+].[K+].C(Cl)Cl.CO>CN(C=O)C>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][C:16]=1[CH:17]([CH3:19])[CH3:18])[C:8]([NH:10][C:11](=[NH:13])[NH:12][C:20](=[O:23])[C:7]1[CH:14]=[CH:15][C:16]([CH:17]([CH3:18])[CH3:19])=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=1)=[O:9])(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21226129Dichloromethane methanolHCID 178439180HCID 178439180, compound

Product 1

HCID 153274983HCID 153274983, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The acid chloride 1 a) and 3.9 g of 3-methylsulfonyl-4-i-propylbenzoylguanidine are dissolved in 50 ml of DMF, and 3.4 g of K2CO3 are then added. The mixture is stirred at RT for 4 h and then left to stand overnight. The solution is subsequently concentrated and the residue stirred up in 200 ml of water. The solid is filtered off and washed with 100 ml of water. This solid is then dissolved in 100 ml of EA and washed 1× with 10 ml of 1N HCl and then 1× with 50 ml of NaCl solution. Drying takes place over Na2SO4 and the solvent is removed in vacuo. A yellow solid is obtained which is purified by being titurated twice with 20 ml of diethyl ether and subsequently being filtered off. The product is dried in vacuo and 1.9 g are obtained of a white solid, mp 218-221° C. Rf (CH2Cl2/MeOH 20:1)=0.57 MS (ES):508 (M+1)

Workup

  1. waitleft
  2. waitto stand overnight
  3. concentrationThe solution is subsequently concentrated
  4. stirringthe residue stirred up in 200 ml of water
  5. filtrationThe solid is filtered off
  6. washwashed with 100 ml of water
  7. dissolutionThis solid is then dissolved in 100 ml of EA
  8. washwashed 1× with 10 ml of 1N HCl
  9. customDrying
  10. customthe solvent is removed in vacuo
  11. customA yellow solid is obtained which
  12. customis purified
  13. filtrationsubsequently being filtered off
  14. customThe product is dried in vacuo and 1.9 g
  15. customare obtained of a white solid, mp 218-221° C

Sources & evidence

ORD record
ord-26622921ffcd474db1578efdeb5e5183
Source dataset
uspto-grants-2003_10
Patent number
US06632840B1

Reaction notes

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