4-Chlorobenzenesulfonyl chloride → HCID 66973638, compound

HRID 1469120Notes

Reaction equation

HRID 1469120 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[C:14]([F:15])=[CH:13][NH:12][C:11](=[O:16])[N:10]=2)=[O:7])=[CH:4][CH:3]=1.CCN(CC)CC.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[C:14]([F:15])=[CH:13][N:12]([S:33]([C:30]3[CH:31]=[CH:32][C:27]([Cl:26])=[CH:28][CH:29]=3)(=[O:35])=[O:34])[C:11](=[O:16])[N:10]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 178522604HCID 178522604, compound

Product 1

HCID 66973638HCID 66973638, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4-chloro-N-(5-fluoro-2-oxo-1,2-dihydropyrimid-4-yl)benzamide (0.10 g, 0.37 mmol) in CH2Cl2 (4 mL) were added Et3N (0.08 g, 0.82 mmol) and 4-chlorobenzenesulfonyl chloride (0.087 g, 0.41 mmol) at 0° C., and the resulting mixture was warmed to room temperature and stirred for 3 h. The reaction was diluted with CH2Cl2 (10 mL) and washed with brine. The phases were separated and the organic phase was dried over sodium sulfate (Na2SO4), filtered, and concentrated to an amber oil (0.295 g). Purification by normal phase chromatography (12 g SiO2; gradient, 0 to 35% EtOAc/hexanes) afforded 4-chloro-N-[1-(4-chlorobenzenesulfonyl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl]benzamide (0.025 g, 26%) as a white solid: mp 169-172° C.; 1H NMR (300 MHz, CDCl3) δ 12.59 (s, 1H), 8.29-8.15 (m, 3H), 8.05 (d, J=8.8 Hz, 2H), 7.59 (d, J=8.7 Hz, 2H), 7.42 (d, J=8.6 Hz, 2H); ESIMS m/z 442 ([M+H]+), 440 ([M−H]−).

Workup

  1. washwashed with brine
  2. customThe phases were separated
  3. dry with materialthe organic phase was dried over sodium sulfate (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to an amber oil (0.295 g)
  6. customPurification by normal phase chromatography (12 g SiO2; gradient, 0 to 35% EtOAc/hexanes)

Sources & evidence

ORD record
ord-092f25f7d7d44901993645e836d67e94
Source dataset
uspto-grants-2015_04
Patent number
US09006259B2

Reaction notes

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