1-(Chloromethoxy)-2-methoxyethane → N-(3-acetyl-2,4-difluoro-phenyl)-2,5-difluoro-N-(2-methoxy-ethoxymethyl)-benzene-sulfonamide

HRID 45896Notes

Reaction equation

HRID 45896 reaction equation
[C:1]([C:4]1[C:5]([F:23])=[C:6]([NH:11][S:12]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[F:22])(=[O:14])=[O:13])[CH:7]=[CH:8][C:9]=1[F:10])(=[O:3])[CH3:2].CCN(C(C)C)C(C)C.[CH3:33][O:34][CH2:35][CH2:36][O:37][CH2:38]Cl>C(Cl)Cl>[C:1]([C:4]1[C:5]([F:23])=[C:6]([N:11]([CH2:33][O:34][CH2:35][CH2:36][O:37][CH3:38])[S:12]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[F:22])(=[O:14])=[O:13])[CH:7]=[CH:8][C:9]=1[F:10])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531DiisopropylethylamineHCID 67184503HCID 67184503, compound

Product 1

HCID 58302704N-(3-acetyl-2,4-difluoro-phenyl)-2,5-difluoro-N-(2-methoxy-ethoxymethyl)-benzene-sulfonamideYield 62.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-(3-acetyl-2,4-difluoro-phenyl)-2,5-difluoro-benzenesulfonamide (2.88 g, 8.293 mmol) was dissolved in dry DCM (75 mL) under nitrogen atmosphere. DIPEA (1.55 mL, 9.12 mmol, 1.1 eq) was then added, followed by 2-methoxyethoxymethyl chloride (0.98 mL, 9.12 mmol, 1.1 eq) and the mixture was stirred at room temperature for 1 h. It was then diluted with DCM and washed with water and brine, dried over Na2SO4 and evaporated to dryness. The crude product was purified by chromatography on silica gel (n-hexane/ethyl acetate 7:3) to give 2.25 g (62%) of N-(3-acetyl-2,4-difluoro-phenyl)-2,5-difluoro-N-(2-methoxy-ethoxymethyl)-benzene-sulfonamide as a yellow oil.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness
  4. customThe crude product was purified by chromatography on silica gel (n-hexane/ethyl acetate 7:3)

Sources & evidence

ORD record
ord-fe6e1aa728a342208a1ca474b1c8918e
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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