Water → HCID 10067305, compound

HRID 1884880Notes

Reaction equation

HRID 1884880 reaction equation
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[C:5]([OH:17])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:24][N:25]([CH2:29][CH2:30]Cl)[CH2:26][CH2:27][Cl:28].Cl.O>CN(C)C=O>[Cl:28][CH2:27][CH2:26][N:25]([CH2:29][CH2:30][O:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[C:5]([OH:17])=[CH:4][CH:3]=1)[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 5935Nitrogen mustard hydrochlorideHCID 11430Potassium CarbonateHCID 235049441,4-Dihydroxy-9H-thioxanthen-9-one

Product 1

HCID 10067305HCID 10067305, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 0.5 g of 1,4-dihydroxythioxanthone in 20 ml of dimethylformamide is stirred for 0.5 h at room temperature with 6 g of potassium carbonate under anhydrous conditions. Mechlorethamine hydrochloride (0.4 g) is then added and the heterogeneous mixture was stirred for 12 h at 50° C. Water is added and the mixture extracted with ethyl acetate. The ethyl acetate solution is washed with water, dried with sodium sulfate, passed through a plug of alumina and concentrated under vacuum to produce 0.4 g (55%).

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. washThe ethyl acetate solution is washed with water
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customto produce 0.4 g (55%)

Sources & evidence

ORD record
ord-44a09621dacc41b8b577e344a03877b2
Source dataset
uspto-grants-2004_07
Patent number
US06767919B2

Reaction notes

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