Water → HCID 10527426, compound

HRID 2226209Notes

Reaction equation

HRID 2226209 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)-1-[[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]ethanesulfonamide, amide, 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-6a15399d2e4d4b399f94dadf2b193f94
Source dataset
uspto-grants-1994_09
Patent number
US05346917

Reaction notes

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