Chloromethyl Methyl Ether → HCID 10152618, compound

HRID 2218200Notes

Reaction equation

HRID 2218200 reaction equation
C(N(CC)C(C)C)(C)C.[CH3:10][O:11][CH2:12]Cl.Cl.[C:15]([N:18]1[C:22]2[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:21]=2[S:20][CH:19]1[C:28]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:29]=1[O:36][CH2:37][CH2:38][CH2:39][N:40]([CH2:44][CH2:45][OH:46])[CH:41]([CH3:43])[CH3:42])(=[O:17])[CH3:16].C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:15]([N:18]1[C:22]2[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:21]=2[S:20][CH:19]1[C:28]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:29]=1[O:36][CH2:37][CH2:38][CH2:39][N:40]([CH:41]([CH3:43])[CH3:42])[CH2:44][CH2:45][O:46][CH2:12][O:11][CH3:10])(=[O:17])[CH3:16]

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 21942813HCID 21942813, compound

Product 1

HCID 10152618HCID 10152618, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N-Diisopropylethylamine (0.18 ml, 1.01 mmol) and chlorodimethyl ether (0.05 ml, 0.55 mmol) were added to a solution of 3-acetyl-6-chloro-2-[2-(3-(N-(2-hydroxyethyl)-N-isopropylamino)-propoxy)-5-methoxyphenyl]benzothiazoline hydrochloride (235 mg, 0.46 mmol) in methylene chloride (2.0 ml) under ice-cooling. The mixture was stirred at room temperature for 3.5 hours, then a saturated aqueous sodium hydrogencarbonate solution (50 ml) was added to the reaction mixture, and the whole was extracted with ethyl acetate (50 ml). The ethyl acetate layer was washed with saturated brine (50 ml) and dehydrated with anhydrous magnesium sulfate, and ethyl acetate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (mobile phase: chloroform/methanol=20/1) to give 124 mg (52%) of the target compound.

Workup

  1. temperaturecooling
  2. extractionthe whole was extracted with ethyl acetate (50 ml)
  3. washThe ethyl acetate layer was washed with saturated brine (50 ml)
  4. concentrationwas concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (mobile phase: chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-82f71d7faf7946a5a2269697408f4bb0
Source dataset
uspto-grants-2008_08
Patent number
US07410987B2

Reaction notes

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