Triethylamine → HCID 591044, compound

HRID 1167002Notes

Reaction equation

HRID 1167002 reaction equation
[CH2:1]([NH2:11])[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[CH3:19][S:20]([NH:11][CH2:1][C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 75799Benzo-1,3-dioxole-5-methylamine

Product 1

HCID 591044HCID 591044, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of piperonylamine (6.07 g, 38.95 mmol) and triethylamine (5.37 g, 53.12 mmol) in dichloromethane (100 ml) at 0° C. was added methanesulfonyl chloride (4.14 g, 35.41 mmol). The reaction was stirred at 0° C. for 1 hour. The mixture was then diluted with dichloromethane (100 ml) and washed with 1 N HCl (2×100 ml). The organic layer was dried (MgSO4), the solid was filtered and the filtrate was concentrated to give N-(3,4-methylenedioxy)benzyl-methanesulfonamide as a grey solid (8.4 g, 92% yield).

Workup

  1. washwashed with 1 N HCl (2×100 ml)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationthe solid was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0741f4cc32b24063b23077be1618e702
Source dataset
uspto-grants-2003_09
Patent number
US06613804B2

Reaction notes

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