Water → HCID 10505924, compound

HRID 1377795Notes

Reaction equation

HRID 1377795 reaction equation
[CH2:1]([N:3]([CH2:25][CH3:26])[CH2:4][CH2:5][NH:6][C:7]1[C:20]2[C:19](=[O:21])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([Br:22])[CH:17]=3)[S:12][C:11]=2[C:10]([CH2:23][NH2:24])=[CH:9][CH:8]=1)[CH3:2].[CH3:27][S:28](Cl)(=[O:30])=[O:29].O.[OH-].[Na+]>N1C=CC=CC=1>[CH2:25]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][NH:6][C:7]1[C:20]2[C:19](=[O:21])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([Br:22])[CH:17]=3)[S:12][C:11]=2[C:10]([CH2:23][NH:24][S:28]([CH3:27])(=[O:30])=[O:29])=[CH:9][CH:8]=1)[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 10550788HCID 10550788, compound

Product 1

HCID 10505924HCID 10505924, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

1-[[2-(Diethylamino)ethyl]amino]-4-(aminomethyl)-7-bromothioxanthen-9-one (1 g, 2.3 mmol) in 11.5 mL of dry pyridine under nitrogen was stirred in an ice bath for 15 min and 0.2 mL (2.6 mmol) of methanesulfonyl chloride in chilled pyridine was added dropwise and the mixture was stirred at room temperature. The reaction mixture was poured into 200 mL of water, added 0.19 g of sodium hydroxide in ice/water, and extracted into chloroform. The organic layer was washed with water (2x) and brine, and dried over anhydrous sodium sulfate. The mixture was filtered, concentrated in vacuo and the residue was stirred in ether, filtered, and dried to afford 1.02g of N-[[1-[[2-(diethylamino)ethyl]amino]-7-bromo -9-oxothioxanthen-4-yl]methyl]-methanesulfonamide, m.p. 134°-139° C.

Workup

  1. extractionextracted into chloroform
  2. washThe organic layer was washed with water (2x) and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated in vacuo
  6. stirringthe residue was stirred in ether
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-21a33f0ddcdf432b852f8b741bb9e8d4
Source dataset
uspto-grants-1997_09
Patent number
US05665760

Reaction notes

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