Triethylamine → 4-[2-Chloromethyl-4-phenyloxazol-5-yl]benzenesulfonamide

HRID 1839551Notes

Reaction equation

HRID 1839551 reaction equation
O[CH2:2][C:3]1[O:4][C:5]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.C(N(CC)CC)C.[Cl-].[Li+].CS([Cl:37])(=O)=O>O1CCCC1.C(OCC)(=O)C>[Cl:37][CH2:2][C:3]1[O:4][C:5]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 433294Lithium ChlorideHCID 222462434-[2-Hydroxymethyl-4-phenyloxazol-5-yl]benzenesulfonamide

Product 1

HCID 222463454-[2-Chloromethyl-4-phenyloxazol-5-yl]benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-[2-hydroxymethyl-4-phenyloxazol-5-yl]benzenesulfonamide (Step 2) (1.0 g, 3 mmol) and triethylamine (0.61 g, 6 mmol) was stirred in tetrahydrofuran (100 mL) at 0° C. Lithium chloride (0.25 g, 6 mmol) was added, followed by the dropwise addition of methanesulfonyl chloride (0.38 g, 3.3 mmol). After stirring for 3 h from 0° C. to 25° C., ethyl acetate (100 mL) was added, and the mixture was washed with 1N hydrochloric acid, brine and water, dried over magnesium sulfate, filtered, and concentrated. The crude product was purified by flash column chromatography on silica gel eluting with a 1:1 mixture of ethyl acetate: hexanes. The appropriate fractions were concentrated to a clear oil which solidified upon standing to give 4-[2-chloromethyl-4-phenyloxazol-5-yl]benzenesulfonamide as a white solid which was used in the next step without further purification or characterization.

Workup

  1. washthe mixture was washed with 1N hydrochloric acid, brine and water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by flash column chromatography on silica gel eluting with a 1:1 mixture of ethyl acetate
  6. concentrationThe appropriate fractions were concentrated to a clear oil which

Sources & evidence

ORD record
ord-c3b8ce5af19c4468bc633cc2de318c48
Source dataset
uspto-grants-2004_01
Patent number
US06677364B2

Reaction notes

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