Water → HCID 10527426, compound

HRID 1769182Notes

Reaction equation

HRID 1769182 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 (2×) 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, 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 (2×) 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-5a3e3e856e724a928a827054e97c8a50
Source dataset
uspto-grants-1995_01
Patent number
US05380749

Reaction notes

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