Acetone → m-AMSA methanesulfonate

HRID 482685

Reaction equation

HRID 482685 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=2[N:17]=[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=12.CC(C)=[O:31]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=12.[CH3:28][S:25]([O-:31])(=[O:27])=[O:26]

Participants

3

Reactant 2

HCID 180AcetoneHCID 2179Amsacrine

Product 1

HCID 86740667m-AMSA methanesulfonate

Procedure

The m-AMSA methanesulfonate salt was prepared by slurrying 1 g of m-AMSA base in 125 ml of acetone for 20 minutes. The resulting near solution was vacuum filtered to remove undissolved solids. The solids remaining in the filter were washed with 10 ml of acetone and the wash solution was added to the original filtrate. To the above solution of m-AMSA base there was added with rapid stirring 0.24 ml of methanesulfonic acid over a three minute interval. Crystals formed and the mixture was stirred five additional minutes. The crystals were then vacuum filtered, washed with two 20 ml portions of acetone and vacuum dried at 50° C. for 24 hours to give 1.18 g of m-AMSA methanesulfonate (1:1) salt.

Workup

  1. customfor 20 minutes
  2. filtrationfiltered
  3. customto remove undissolved solids
  4. washwere washed with 10 ml of acetone
  5. additionthe wash solution was added to the original filtrate
  6. additionTo the above solution of m-AMSA base there was added
  7. customCrystals formed
  8. stirringthe mixture was stirred five additional minutes
  9. filtrationvacuum filtered
  10. washwashed with two 20 ml portions of acetone and vacuum
  11. customdried at 50° C. for 24 hours

Sources & evidence

ORD record
ord-24eeac5b8d874057af729d897a646fa4
Source dataset
uspto-grants-1986_03
Patent number
US04575509

Linked notes

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