Chloromethyl Methyl Ether → HCID 11472176, compound

HRID 1059274Notes

Reaction equation

[N:1]1[C:10]2[NH:9][C:8]3[CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=[CH:14][C:7]=3[S:6][C:5]=2[N:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:21][O:22][CH2:23]Cl>CN(C)C=O>[CH3:21][O:22][CH2:23][N:9]1[C:8]2[CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=[CH:14][C:7]=2[S:6][C:5]2[N:4]=[CH:3][CH:2]=[N:1][C:10]1=2

Participants

Conditions

Temperature: -5 °C

Procedure

415 g of methyl 10H-pyrazino[2,3-b][1,4]benzothiazine-8-carboxylate was suspended in 2.5 l of N,N-dimethylformamide in a nitrogen atmosphere. Then 66 g of sodium hydride (oily: 60% or more) was added in portions thereto while maintaining the mixture at −10 to 0° C. Then the resulting mixture was stirred for 1 hour. Next, 110 g of chloromethyl methyl ether was dropped thereinto while maintaining the mixture at a temperature not exceeding 5° C. After the completion of the reaction, the reaction mixture was poured into ice, extracted with methylene chloride twice, washed with water and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, diisopropyl ether was added to the residues and the crystals thus precipitated were taken up by filtration to thereby give 335 g of the title compound as yellow crystals.

Workup

temperaturewhile maintaining the mixture at a temperature not
customexceeding 5° C
customAfter the completion of the reaction
additionthe reaction mixture was poured into ice
extractionextracted with methylene chloride twice
washwashed with water
dry with materialdried over anhydrous sodium sulfate
distillationAfter distilling off the solvent under reduced pressure, diisopropyl ether
additionwas added to the residues
customthe crystals thus precipitated
filtrationwere taken up by filtration

Sources & evidence

ORD record: ord-68289f0f89914ee9bd1a667f18be6a3b
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518423B1

Reaction notes

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