Methanesulfonyl chloride → HCID 19813442, compound

HRID 345022Notes

Reaction equation

HRID 345022 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][N:7]([CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])=[CH:24][CH:23]=1)[CH2:8][C:9]1[O:10][C:11]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][C:12]=2[C:13]=1[CH3:14]>N1C=CC=CC=1>[CH3:6][N:7]([CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][S:29]([CH3:32])(=[O:30])=[O:31])=[CH:24][CH:23]=1)[CH2:8][C:9]1[O:10][C:11]2[CH:18]=[CH:17][C:16]([NH:19][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:15][C:12]=2[C:13]=1[CH3:14]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 19813432HCID 19813432, compound

Product 1

HCID 19813442HCID 19813442, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulphonyl chloride (0.21 g, 1.85 mmole) was added dropwise to a solution of N-methyl-N-(3-methyl-5-aminobenzofur-2-ylmethyl)-4-methanesulphonamidophenethylamine (see Preparation 10B - 0.78 g, 1.68 mmole) in pyridine (7 ml) and the solution was then stirred at room temperature for 60 hours. The solvent was evaporated and the residue triturated with toluene. The toluene was decanted, the residue stirred with aqueous sodium bicarbonate, and the precipitate collected by filtration and recrystallised from methanol to give the title compound, yield 0.38 g, m.p. 142°-143.5°.

Workup

  1. customThe solvent was evaporated
  2. customthe residue triturated with toluene
  3. customThe toluene was decanted
  4. stirringthe residue stirred with aqueous sodium bicarbonate
  5. filtrationthe precipitate collected by filtration
  6. customrecrystallised from methanol

Sources & evidence

ORD record
ord-1bd76241bd0b47a6a9dd3a8dec90aa5d
Source dataset
uspto-grants-1991_10
Patent number
US05055473

Reaction notes

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