Hydrochloric Acid → N-butyl-5-chloro-N-methyl-pentanesulfonamide

HRID 2396695Notes

Reaction equation

HRID 2396695 reaction equation
[CH2:1]([NH:5][CH3:6])[CH2:2][CH2:3][CH3:4].[Cl:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][S:13](Cl)(=[O:15])=[O:14].C(N(CC)CC)C.Cl>C(Cl)Cl>[CH2:1]([N:5]([CH3:6])[S:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][Cl:7])(=[O:15])=[O:14])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8068N-MethylbutylamineHCID 8471TriethylamineHCID 12589202HCID 12589202, compound

Product 1

HCID 19711033N-butyl-5-chloro-N-methyl-pentanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

0.47 ml of N-butylmethylamine were added under an inert gas atmosphere to a solution of 410 mg of 5-chloropentane sulfonyl chloride in 10 ml of methylene chloride. The temperature rose from 13° C. to 26° C., and then after cooling to 0 to 5° C., 0.55 ml of triethylamine were added. The mixture was stirred at ambient temperature for 2 hours and the reaction medium was poured into an aqueous solution of 1M hydrochloric acid, extracted with methylene chloride, washed with water, then with a saturated aqueous solution of sodium chloride, dried and evaporated to dryness under reduced pressure to obtain 486 mg of the expected product.

Workup

  1. customrose from 13° C. to 26° C.
  2. extractionextracted with methylene chloride
  3. washwashed with water
  4. dry with materialwith a saturated aqueous solution of sodium chloride, dried
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f05759d986ca4329897c7a8e378608e8
Source dataset
uspto-grants-1996_02
Patent number
US05494907

Reaction notes

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