Methanesulfonyl chloride → HCID 10433970, compound

HRID 467081Notes

Reaction equation

HRID 467081 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][N:7]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1)[CH2:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:12]=2[CH:13]=1>N1C=CC=CC=1>[CH3:6][N:7]([CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([NH:27][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:25][CH:26]=1)[CH2:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([NH:18][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:14][C:12]=2[CH:13]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 15735403HCID 15735403, compound

Product 1

HCID 10433970HCID 10433970, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulphonyl chloride (0.76 g, 6.6 mmole) was added dropwise to a solution of N-methyl-N-(5-aminobenzofur-2-ylmethyl)-4-aminophenethylamine (see Preparation 3--0.9 g, 3.0 mmole) in pyridine (25 ml) and the mixture was stirred at room temperature for 18 hours. The solvent was then evaporated and the residue diluted with aqueous sodium bicarbonate and extracted three times with methylene chloride. The combined organic extracts were dried (MgSO4) and evaporated, and the residue was purified by chromatography on silica eluting with ethyl acetate. The product-containing fractions were combined, evaporated and the resulting solid was recrystallised from ethyl acetate/methanol to give the title compound, yield 0.35 g, m.p. 177°-179°.

Workup

  1. customThe solvent was then evaporated
  2. additionthe residue diluted with aqueous sodium bicarbonate
  3. extractionextracted three times with methylene chloride
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customevaporated
  6. customthe residue was purified by chromatography on silica eluting with ethyl acetate
  7. customevaporated
  8. customthe resulting solid was recrystallised from ethyl acetate/methanol

Sources & evidence

ORD record
ord-fbb7e7ed791148f1842197a4cf98ccb6
Source dataset
uspto-grants-1992_10
Patent number
US05158964

Reaction notes

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