Methyl iodide → HCID 86693320, compound

HRID 575291Notes

Reaction equation

HRID 575291 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:5]2[O:6][CH2:7][CH:8]([OH:19])[C:9]3[S:13][C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:11][C:10]=3[C:4]=2[CH:3]=1.I[CH3:23]>ClCCl>[Br:1][C:2]1[CH:21]=[CH:20][C:5]2[O:6][CH2:7][CH:8]([O:19][CH3:23])[C:9]3[S:13][C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:11][C:10]=3[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 86693321HCID 86693321, compound

Product 1

HCID 86693320HCID 86693320, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of ethyl 9-bromo-4-hydroxy-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate (500 mg, 1.35 mmol, 1.00 equiv), Ag2O (1.247 g, 4.00 equiv), and iodomethane (763 mg, 5.38 mmol, 4.00 equiv) in dichloromethane (5 mL) was stirred for 3 h at 50. The reaction was quenched with 10 mL of brine, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:20) to give 150 mg (29%) of the titled compound as a white solid; LC-MS (ES, m/z) 384, 386[M+H]+.

Workup

  1. customThe reaction was quenched with 10 mL of brine
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:20)

Sources & evidence

ORD record
ord-3e566723d68d42e2a7e86bbb836d690b
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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