Dichloromethane → HCID 18942238, compound

HRID 355420Notes

Reaction equation

HRID 355420 reaction equation
CS(Cl)(=O)=O.O[C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH3:21])[C:12]3[C:17]([S:18][C:19]=2[CH:20]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3.C(N(CC)CC)C.[Cl:29][CH2:30]Cl>O>[Cl:29][CH2:30][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH3:21])[C:12]3[C:17]([S:18][C:19]=2[CH:20]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54514826HCID 54514826, compound

Product 1

HCID 18942238HCID 18942238, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

With ice-cooling, methanesulfonyl chloride (3.9 ml, 50 mmol) was added dropwise to a mixture of 3-hydroxy-10-methylphenothiazine (10.9 g, 45 mmol), triethylamine (8.2 ml, 59 mmol) and dichloromethane (80 ml), and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture and the reaction product was extracted with chloroform. The extract was washed with a saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution in that order, dried over anhydrous magnesium sulfate, and concentrated under a reduced pressure to give the title compound (8.09 g, 30.9 mmol, 69%) as yellow crystals.

Workup

  1. temperatureWith ice-cooling
  2. extractionthe reaction product was extracted with chloroform
  3. washThe extract was washed with a saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution in that order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-32306c9741f845a19c843474058abf44
Source dataset
uspto-grants-1998_11
Patent number
US05830902

Reaction notes

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