Methacryloyl chloride → HCID 22181556, compound

HRID 1796315Notes

Reaction equation

HRID 1796315 reaction equation
[C:1]([NH:5][S:6]([C:9]1[C:10]([C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[C:17]([F:22])[CH:16]=2)=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].[CH3:28][C:29](=[CH2:33])[C:30](Cl)=[O:31]>C(OCC)(=O)C>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:30](=[O:31])[C:29]([CH3:33])=[CH2:28])=[C:17]([F:22])[CH:16]=1)(=[O:8])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 13528Methacryloyl chlorideHCID 516892Sodium BicarbonateHCID 108532844'-Amino-3'-fluoro-biphenyl-2-sulfonic acid tert-butylamide

Product 1

HCID 22181556HCID 22181556, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 4′-Amino-3′-fluoro-biphenyl-2-sulfonic acid tert-butylamide (5.000 g, 15.51 mmoles) at room temperature in ethyl acetate (50 ml) was added saturated sodium bicarbonate, aqueous, 50 ml and then 2-methyl-acryloyl chloride (1.25 equiv.). Stirred for 2 hours then added a further 1 ml of the acid chloride. After 2 hours an aliquot showed product by NMR. Product seems to co-run with starting material. Extracted into ethyl acetate, washed with brine, dried MgSO4, and then concentrated in vacuo. Collected some crystalline product from ethyl acetate hexane, 0.48 g. Columned mother liquor to afford product. Combined with previously crystallized fraction to afford N-(2′-tert-Butylsulfamoyl-3-fluoro-biphenyl-4-yl)-2-methyl-acrylamide (4.520 g). APCI (AP+): 391 (M+H)+.

Workup

  1. waitAfter 2 hours an aliquot showed product by NMR
  2. extractionExtracted into ethyl acetate
  3. washwashed with brine, dried MgSO4
  4. concentrationconcentrated in vacuo
  5. customCollected some crystalline product from ethyl acetate hexane, 0.48 g
  6. customColumned mother liquor to afford product

Sources & evidence

ORD record
ord-f22b05800e714a4f806f48fa1141dac6
Source dataset
uspto-grants-2006_04
Patent number
US07030141B2

Reaction notes

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