Water → HCID 178483367, compound

HRID 1106503Notes

Reaction equation

HRID 1106503 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].CC(C)([O-])C.[K+].[Cl:12][C:13]1[CH:22]=[C:21]([O:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][N:32]([CH3:34])[CH3:33])=[CH:26][CH:25]=2)[C:20]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:19][C:14]=1[C:15](OC)=[O:16].O>CN(C=O)C>[Cl:12][C:13]1[CH:22]=[C:21]([O:23][C:24]2[CH:25]=[CH:26][C:27]([CH2:30][CH2:31][N:32]([CH3:34])[CH3:33])=[CH:28][CH:29]=2)[C:20]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:19][C:14]=1[C:15]([NH:4][C:3]([NH2:5])=[NH:2])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 5742Guanidine HydrochlorideHCID 18788900Methyl 2-chloro-4-(4-(2-dimethylaminoethyl)phenoxy)-5-methylsulfonylbenzoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 178483367HCID 178483367, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

268 mg of guanidine hydrochloride were dissolved in 3 ml of DMF and a solution of 286 mg of potassium t-butoxide in 3 ml of DMF is added. The mixture was stirred at RT for 3 hours, then a solution of 210 mg of methyl 2-chloro-4-(4-(2-dimethylaminoethyl)phenoxy)-5-methylsulfonylbenzoate in 4 ml of DMF was added. The mixture was stirred at RT for 3 hours and allowed to stand at RT for 18 hours. The mixture was poured onto 150 ml of water and extracted 3 times using 100 ml of EA each time. The organic phase was dried over Na2SO4 and the solvent was removed in vacuo. 230 mg of a glassy solid were obtained.

Workup

  1. stirringThe mixture was stirred at RT for 3 hours
  2. waitto stand at RT for 18 hours
  3. extractionextracted 3 times
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6c1ee9ab70fc455f8afcc5e57d3b38b6
Source dataset
uspto-grants-2000_05
Patent number
US06057322

Reaction notes

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