Hydrochloric Acid → HCID 178427991, compound

HRID 501252Notes

Reaction equation

HRID 501252 reaction equation
CC([O-])(C)C.[K+].[Cl-].[NH2:8][C:9]([NH2:11])=[NH2+:10].[F:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:23][S:22](=[O:25])(=[O:24])[N:21]([C:26]3[C:35]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:34][C:29]([C:30](OC)=[O:31])=[C:28]([CH3:40])[CH:27]=3)[CH2:20]2)=[CH:15][CH:14]=1.Cl>CN(C=O)C.O>[F:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:23][S:22](=[O:24])(=[O:25])[N:21]([C:26]3[C:35]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:34][C:29]([C:30]([NH:10][C:9]([NH2:11])=[NH:8])=[O:31])=[C:28]([CH3:40])[CH:27]=3)[CH2:20]2)=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5460839Carbamimidoylazanium ChlorideHCID 23665647Potassium tert-butoxideHCID 68462085Methyl 4-[4-(4-fluorophenyl)-1,1-dioxoisothiazolidin-2-yl]-5-methanesulfonyl-2-methylbenzoate

Product 1

HCID 178427991HCID 178427991, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

44.48 g of KOtBu were dissolved in 800 ml of anhydrous DMF and, at RT, 45.44 g of guanidinium chloride were added. After stirring at RT for 1 hour, the solution was poured into a solution of 35.00 g of methyl 4-[4-(4-fluoro-phenyl)-1,1-dioxoisothiazolidin-2-yl]-5-methanesulfonyl-2-methylbenzoate in 300 ml of anhydrous DMF. The mixture was then stirred at RT for 5 hours. It was then poured into 2 l of water, adjusted to pH=8 with aqueous HCl solution and extracted 5 times with 300 ml of EA each time. After drying over MgSO4, the solvent was removed in vacuo.

Workup

  1. stirringThe mixture was then stirred at RT for 5 hours
  2. extractionextracted 5 times with 300 ml of EA each time
  3. dry with materialAfter drying over MgSO4
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-01042a53b9084c0f854d2050f62c2c8d
Source dataset
uspto-grants-2010_08
Patent number
US07772262B2

Reaction notes

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