Methanesulfonyl chloride → HCID 53981302, compound

HRID 464036Notes

Reaction equation

HRID 464036 reaction equation
[CH2:1]([N:3]([CH2:15][CH3:16])[CH2:4][CH:5]=[CH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)[CH3:2].[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[CH2:15]([N:3]([CH2:1][CH3:2])[CH2:4][CH:5]=[CH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][S:18]([CH3:17])(=[O:20])=[O:19])=[CH:10][CH:9]=1)[CH3:16]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 54150638HCID 54150638, compound

Product 1

HCID 53981302HCID 53981302, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 3.5 g (0.014 mole) N,N-diethyl-4-(4-aminophenyl)-2-buten-1-amine in 50 ml of methylene chloride, chill to about 0° C. To this slowly add 1.5 ml (0.019 mole) of methanesulfonyl chloride. Stir at room temperature 1 hr and then wash with 2×50 ml of 10% NaOH. Wash the sodium hydroxide extracts with 1×100 ml of ether and then acidify to pH 10 with concentrated HCl. Extract with 2×100 ml methylene chloride and dry the methylene chloride extracts over Na2SO4. Evaporate to dryness to yield the title compound.

Workup

  1. washwash with 2×50 ml of 10% NaOH
  2. washWash the sodium hydroxide
  3. extractionExtract with 2×100 ml methylene chloride
  4. dry with materialdry the methylene chloride
  5. customEvaporate to dryness

Sources & evidence

ORD record
ord-ec88621148d9491880f6c81024885c1e
Source dataset
uspto-grants-1985_10
Patent number
US04545995

Reaction notes

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