Water → HCID 10527426, compound

HRID 1377787Notes

Reaction equation

HRID 1377787 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]([CH2:24][CH3:25])[CH2:22][CH3:23])=[CH:5][CH:4]=1.[CH2:26]([S:28](Cl)(=[O:30])=[O:29])[CH3:27].O.[OH-].[Na+]>N1C=CC=CC=1>[CH2:22]([N:21]([CH2:24][CH3:25])[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:28]([CH2:26][CH3:27])(=[O:30])=[O:29])=[CH:4][CH:5]=1)[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 11667Ethanesulfonyl chlorideHCID 14798Sodium HydroxideHCID 9998338HCID 9998338, compound

Product 1

HCID 10527426HCID 10527426, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 2.5 g of 4-(aminomethyl)-l-[[2-(diethylamino) ethyl]amino]-thioxanthen-9-one (prepared by the method described in Example 4) in 30 mL of pyridine was cooled in an ice bath for 15 min and 0.95 g of ethanesulfonyl chloride in 5 mL of pyridine was added rapidly dropwise and the reaction mixture was stirred at room temperature for 1 h. The mixture was poured into 75 mL of water containing 0.75 g of NaOH, extracted into chloroform, the organic layer was washed with water (2x) and brine, and dried over sodium sulfate. The mixture was concentrated in vacuo and the residue was stirred in ether and dried (40° C./0.1 mm) to afford 1.7 g of N-[[1-[[2-(diethylamino)ethyl]amino]-9-oxothioxanthen-4-yl]methyl]ethane-sulfonamide, m.p. 105° C. (dec.). The sulfonamide was dissolved in methanol and treated with methanesulfonic acid in methanol to afford 1.61 g (42%) of the methanesulfonate salt, m.p. 135° C. (dec.).

Workup

  1. temperaturewas cooled in an ice bath for 15 min
  2. extractionextracted into chloroform
  3. washthe organic layer was washed with water (2x) and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationThe mixture was concentrated in vacuo
  6. stirringthe residue was stirred in ether
  7. customdried (40° C./0.1 mm)

Sources & evidence

ORD record
ord-9c882b643eba41499f7b9dbf72c8f7e4
Source dataset
uspto-grants-1997_09
Patent number
US05665760

Reaction notes

Loading…