Sodium Hydroxide → HCID 13135275, compound

HRID 2412370Notes

Reaction equation

HRID 2412370 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([NH:10][C:11]([NH:13][S:14]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]2Cl)(=[O:16])=[O:15])=[O:12])[N:4]=1.[OH-].[Na+]>CO.O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([NH:10][C:11]([NH:13][S:14]([C:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]=2)(=[O:16])=[O:15])=[O:12])[N:4]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 13135261HCID 13135261, compound

Product 1

HCID 13135275HCID 13135275, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

36.2 g (0.1 mole) of N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-chlorocyclohex-1-ylsulfonamide (see Example 1) were suspended in 300 ml of methanol and 8 g (0.2 mole) of sodium hydroxide dissolved in 40 ml of water were added at room temperature. The reaction mixture was then stirred under reflux for 8 hours, evaporated in vacuo and taken up in 250 ml of water. After filtration and acidification with 2N HCl to pH 5, extraction was carried out with ethyl acetate and then the extracts were dried over sodium sulfate and evaporated. After adding n-hexane, 17.2 g (52.7% of theory) of N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1-cyclohexenylsulfonamide were obtained, having a melting point of 163°-166° C.

Workup

  1. additionwere added at room temperature
  2. temperatureunder reflux for 8 hours
  3. customevaporated in vacuo
  4. filtrationAfter filtration and acidification with 2N HCl
  5. extractionto pH 5, extraction
  6. dry with materialthe extracts were dried over sodium sulfate
  7. customevaporated
  8. additionAfter adding n-hexane

Sources & evidence

ORD record
ord-6f5e783ae2a74177af4679fc1f79473d
Source dataset
uspto-grants-1985_01
Patent number
US04492598

Reaction notes

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