Water → HCID 23051913, compound

HRID 1651428Notes

Reaction equation

HRID 1651428 reaction equation
[CH2:1]([O:5][C:6]1[C:9](=[O:10])[C:8](=[O:11])[C:7]=1[NH:12][CH2:13][CH2:14][CH2:15]O)[CH2:2][CH2:3][CH3:4].[CH3:17][S:18](Cl)(=[O:20])=[O:19].O>N1C=CC=CC=1>[CH2:1]([O:5][C:6]1[C:9](=[O:10])[C:8](=[O:11])[C:7]=1[NH:12][CH2:13][CH2:14][CH2:15][S:18]([CH3:17])(=[O:20])=[O:19])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 15078769HCID 15078769, compound

Product 1

HCID 23051913HCID 23051913, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1-butoxy-2-(3-hydroxypropylamino)-1-cyclobutene-3,4-dione [prepared in Example 7] (1.0 g, 4.4 mmol) in 5 mL of pyridine was cooled to 0° C. and treated dropwise with 0.36 mL (4.6 mmol) of methanesulfonyl chloride. The mixture was stirred at ambient temperature for 1 hour then poured into 80 mL of water and extracted with 20 mL of ethyl acetate. The organic phase was washed 4 times with water, dried and evaporated to give 0.84 g of title compound.

Workup

  1. extractionextracted with 20 mL of ethyl acetate
  2. washThe organic phase was washed 4 times with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-280ae6ce984c4df98935e252bb5353be
Source dataset
uspto-grants-1990_05
Patent number
US04927970

Reaction notes

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