Chloromethyl Methyl Ether → HCID 86719968, compound

HRID 1617328Notes

Reaction equation

HRID 1617328 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[C:7]([C:10]1[CH:19]=[CH:18][C:13]2[NH:14][C:15](=[O:17])[S:16][C:12]=2[CH:11]=1)(=[O:9])[CH3:8].[CH3:20][O:21][CH2:22]Cl.CCOC(C)=O>CN(C)C=O>[C:7]([C:10]1[CH:19]=[CH:18][C:13]2[N:14]([CH2:20][O:21][CH3:22])[C:15](=[O:17])[S:16][C:12]=2[CH:11]=1)(=[O:9])[CH3:8]

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 6890536-Acetyl-2(3H)-benzothiazolone

Product 1

HCID 86719968HCID 86719968, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add cesium carbonate (1.5 Eq; 310.5 mmoles; 101.1 g) to a solution of 6-acetyl-3H-1,3-benzothiazol-2-one (40.0 g, 207 mmoles) in dimethylformamide (690 mL). Add chloromethyl methyl ether (1.3 Eq, 269 mmoles, 20.4 mL) dropwise and stir at room temperature for 18 hr. Transfer to a separatory funnel, add EtOAc (1 L), wash with water (2×200 mL), and then brine (200 mL). Back extract with DCM (300 mL). Dry the combined organic layers over Na2SO4, filter and concentrate. Slurry the concentrate in 200 ml hexanes/EtOAc (75:25), and filter to give 6-acetyl-3-(methoxymethyl)-3H-1,3-benzothiazol-2-one as a white solid (37.0 g, 156 mmoles, 75% yield). LCMS (low) rt=1.68 min., M+1=238.

Workup

  1. washwash with water (2×200 mL)
  2. extractionBack extract with DCM (300 mL)
  3. dry with materialDry the combined organic layers over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate
  6. concentrationconcentrate in 200 ml hexanes/EtOAc (75:25)
  7. filtrationfilter

Sources & evidence

ORD record
ord-919e066cc4f04fc8860b587aa8c0ece3
Source dataset
uspto-grants-2014_07
Patent number
US08765960B2

Reaction notes

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