Methylamine → HCID 54146006, compound

HRID 582460Notes

Reaction equation

HRID 582460 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([CH2:15]Br)[CH:12]=[CH:11][C:10]=1[S:17]([CH3:20])(=[O:19])=[O:18])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:21][NH2:22]>C1COCC1>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([CH2:15][NH:22][CH3:21])[CH:12]=[CH:11][C:10]=1[S:17]([CH3:20])(=[O:19])=[O:18])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 54007580HCID 54007580, compound

Product 1

HCID 54146006HCID 54146006, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At 0° C., 51 g of N-tert-butyl-5-bromomethyl-2-methanesulfonylbenzenesulfonamide (55% by weight A 28.05 g=0.669 mol) dissolved in 250 ml of THF are added to a solution of 59.5 ml (0.69 mol) of a 40% strength aqueous methylamine solution in 150 ml of THF. Stirring is continued at 0-5° C. for 2-3 h. For work-up, the solution is completely concentrated, the residue is taken up in plenty of 2N HCl and extracted with diethyl ether (2×200 ml). The acidic aqueous phase is adjusted to pH 9 with 4N NaOH and extracted with ethyl acetate (3×200 ml). The combined ethyl acetate extracts are washed with water, dried over Na2SO4 and evaporated in vacuo. 17 g (73.7%) of N-tert-butyl-5-methylaminomethyl-2-methanesulfonylbenzenesulfonamide of melting point 76-78° C. are obtained as residue.

Workup

  1. concentrationFor work-up, the solution is completely concentrated
  2. extractionextracted with diethyl ether (2×200 ml)
  3. extractionextracted with ethyl acetate (3×200 ml)
  4. washThe combined ethyl acetate extracts are washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-25bf6935607341aea8623e78e055ddf0
Source dataset
uspto-grants-1999_07
Patent number
US05925596

Reaction notes

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