Water → HCID 9931131, compound

HRID 1377783Notes

Reaction equation

HRID 1377783 reaction equation
[NH2:1][CH2:2][C:3]1[C:16]2[S:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=[O:17])[C:7]=2[C:6]([NH:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])=[CH:5][CH:4]=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26].O.[OH-].[Na+]>N1C=CC=CC=1>[CH3:22][N:21]([CH3:23])[CH2:20][CH2:19][NH:18][C:6]1[C:7]2[C:8](=[O:17])[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[S:15][C:16]=2[C:3]([CH2:2][NH:1][S:25]([CH3:24])(=[O:27])=[O:26])=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 22915318HCID 22915318, compound

Product 1

HCID 9931131HCID 9931131, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

4-(Aminomethyl)-1-[[2-(dimethylamino)ethyl]amino]-thioxanthen-9-one (2 g, 6 mmol) in 30 mL of dry pyridine under nitrogen was stirred at room temperature until the solution was complete. The solution was chilled in an ice-bath and 0.52 mL(6.7 mmol) of methanesulfonyl chloride in chilled pyridine was added dropwise and the mixture was stirred for 1 h at room temperature. The reaction mixture was poured into 500 mL of water containing 0.51 g of sodium hydroxide, extracted into chloroform, the organic layer was washed with water (2x) and brine, and dried over anhydrous sodium sulfate. The mixture was filtered and concentrated in vacuo. The residue (2.5 g) was stirred in either, filtered, and dried to afford 2 g of N-[[1-[[2-(dimethylamino)ethyl]amino]-9-oxothioxanthen-4-yl]methyl]methane-sulfonamide, m.p. 126°-127° C. The free base was dissolved in MeOH and treated with methane sulfonic acid (0.48 g) to afford 2.0 g (67%) of the product as the methanesulfonate salt, m.p. 168° C. (dec.).

Workup

  1. temperatureThe solution was chilled in an ice-bath
  2. extractionextracted into chloroform
  3. washthe organic layer was washed with water (2x) and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated in vacuo
  7. stirringThe residue (2.5 g) was stirred in either,
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-990092b3e90e4f49866c2c0d35c3ac29
Source dataset
uspto-grants-1997_09
Patent number
US05665760

Reaction notes

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