Calcium Sulfate → HCID 13561102, compound

HRID 1589345Notes

Reaction equation

HRID 1589345 reaction equation
S([O-])([O-])(=O)=O.[Ca+2].[CH2:7]([N:11]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1)[CH2:8][CH2:9][CH3:10].[CH3:30][S:31](Cl)(=[O:33])=[O:32]>N1C=CC=CC=1>[CH2:7]([N:11]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][S:31]([CH3:30])(=[O:33])=[O:32])=[CH:18][CH:17]=1)[CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 24497Calcium SulfateHCID 31297Methanesulfonyl chlorideHCID 23316740HCID 23316740, compound

Product 1

HCID 13561102HCID 13561102, compoundYield 114.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
15 °C

Procedure

A 250 ml 3-neck round bottom flask fitted with a thermometer, addition funnel, and calcium sulfate drying tube was charged with 8.5 g (0.027 mol) of N-butyl-N-heptyl-4-aminobenzenebutanamine and 90 ml of dry pyridine. The reaction mixture was cooled to a temperature of about 10°-15° C. and 2.6 ml (0.034 mol) of methanesulfonyl chloride was added thereto while maintaining the temperature below approximate 15° C. The external ice bath was removed and the reaction mixture was stirred overnight at room temperature. The volatiles were evaporated under reduced pressure and the pH of the reaction mixture was raised to about 9 by the addition of water and concentrated ammonium hydroxide. The aqueous solution was extracted four times with chloroform and the organic extracts were combined, washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The organic phase was concentrated to provide 12.246 g of N-[4-[4-(butylheptylamino)butyl]phenyl]methanesulfonamide as an oil.

Workup

  1. additionwas added
  2. customThe external ice bath was removed
  3. customThe volatiles were evaporated under reduced pressure
  4. temperaturethe pH of the reaction mixture was raised to about 9 by the addition of water and concentrated ammonium hydroxide
  5. extractionThe aqueous solution was extracted four times with chloroform
  6. washwashed with a saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-3e229fe1e1294586af7756cafdd5eab4
Source dataset
uspto-grants-1986_02
Patent number
US04569801

Reaction notes

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