Sodium hydride → HCID 58748463, compound

HRID 1366276Notes

Reaction equation

HRID 1366276 reaction equation
[CH2:1]([S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH2:13])(=[O:6])=[O:5])[CH2:2][CH3:3].[H-].[Na+].[Cl:16][C:17]1[N:22]=[C:21](Cl)[C:20]([Cl:24])=[CH:19][N:18]=1.[Cl-].[NH4+]>O.CN(C)C=O>[Cl:16][C:17]1[N:22]=[C:21]([NH:13][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:4]([CH2:1][CH2:2][CH3:3])(=[O:6])=[O:5])[C:20]([Cl:24])=[CH:19][N:18]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 2372592,4,5-TrichloropyrimidineHCID 30186702-(Propane-1-sulfonyl)aniline

Product 1

HCID 58748463HCID 58748463, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(Propane-1-sulfonyl)-phenylamine (3.69 g, 18.5 mmol) of N,N-dimethylformamide (40 mL), sodium hydride (1.48 g, 37 mmol) is added portionwise at 0° C. After stirring, 2,4,5-trichloropyrimidine (2.1 mL, 18.5 mmol) is added. The mixture is stirred at 0° C. for 30 minutes and is further stirred at room temperature for 7 hrs. After adding saturated aqueous ammonium chloride, the mixture is poured into water and extracted twice with ethyl acetate. The organic layer is washed with brine, dried over sodium sulfate, and evaporated in vacuo. The residue is purified by silica gel column chromatography (n-hexane-ethyl acetate gradient) to afford the title compound as colorless solids.

Workup

  1. stirringThe mixture is stirred at 0° C. for 30 minutes
  2. stirringis further stirred at room temperature for 7 hrs
  3. extractionextracted twice with ethyl acetate
  4. washThe organic layer is washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue is purified by silica gel column chromatography (n-hexane-ethyl acetate gradient)

Sources & evidence

ORD record
ord-585eaae4dd07443daf150428ea73942d
Source dataset
uspto-grants-2011_02
Patent number
US07893074B2

Reaction notes

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