Chloromethyl Methyl Ether → (NE)-3-chloro-4-fluoro-N-[1-(methoxymethyl)pyrimidin-4-ylidene]benzenesulfonamide

HRID 1402030Notes

Reaction equation

HRID 1402030 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][N:14]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].C(N(CC)C(C)C)(C)C.[CH3:28][O:29][CH2:30]Cl>C(Cl)Cl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([S:9](/[N:12]=[C:13]2/[N:14]=[CH:15][N:16]([CH2:28][O:29][CH3:30])[CH:17]=[CH:18]/2)(=[O:10])=[O:11])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 594364913-chloro-4-fluoro-N-pyrimidin-4-ylbenzenesulfonamide

Product 1

HCID 59436500(NE)-3-chloro-4-fluoro-N-[1-(methoxymethyl)pyrimidin-4-ylidene]benzenesulfonamideYield 91.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 3-chloro-4-fluoro-N-pyrimidin-4-ylbenzenesulfonamide (Preparation 426, 73 mg, 0.25 mmol) in methylene chloride (2 mL) cooled at 0° C. was added N,N-diisopropylethylamine (0.066 mL, 0.38 mmol) and chloromethyl methyl ether (0.025 mL, 0.28 mmol). After stirring at room temperature for 18 hours, the reaction mixture was diluted with ethyl acetate, washed successively with 1N aqueous sodium hydroxide, water, saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated to give 76 mg (90%) of the title compound as an orange oil and a mixture of three regioisomers that were not separated.

Workup

  1. washwashed successively with 1N aqueous sodium hydroxide, water, saturated aqueous sodium chloride solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3b44a217b2f94f97b65b7904ed9cabec
Source dataset
uspto-grants-2014_12
Patent number
US08907101B2

Reaction notes

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