Chlorotrimethylsilane → HCID 12832226, compound

HRID 1447066Notes

Reaction equation

HRID 1447066 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:17])[C:11](=[CH:15][CH:16]=2)[C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[Si](C)(C)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>ClCCl>[CH3:30][S:31]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][C:10](=[O:17])[C:11](=[CH:15][CH:16]=2)[C:12]([OH:14])=[O:13])=[CH:6][CH:7]=1)(=[O:33])=[O:32]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 129189566-(4-Aminophenyl)-1,2-dihydro-2-oxonicotinic acid

Product 1

HCID 12832226HCID 12832226, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 23.02 g (0.1 mol) of 6-(4-aminophenyl)-1,2-dihydro-2-oxonicotinic acid, 1 L of dichloromethane, and 42.0 ml (0.303 mol) of triethylamine is stirred at 0°-5° and 42.17 ml (0.33 mol) of chlorotrimethylsilane is added. The ice bath is removed and the mixture is stirred at room temperature for 1 hr. The hazy solution is cooled to 10° and 23.8 ml (0.31 mol) of methanesulfonyl chloride is added. The resulting solution is stirred at room temperature for 24 hours and the dichloromethane is evaporated under reduced pressure and 500 ml of water is added to the residue. The mixture is cooled to 10° and the solid is filtered, washed with water, acetonitrile, and ether, and dried to give 29.9 of 6-[4-(methylsulfonylamino)phenyl]-1,2-dihydro-2-oxonicotinic acid; mp>320°.

Workup

  1. customThe ice bath is removed
  2. stirringthe mixture is stirred at room temperature for 1 hr
  3. temperatureThe hazy solution is cooled to 10°
  4. stirringThe resulting solution is stirred at room temperature for 24 hours
  5. customthe dichloromethane is evaporated under reduced pressure and 500 ml of water
  6. additionis added to the residue
  7. temperatureThe mixture is cooled to 10°
  8. filtrationthe solid is filtered
  9. washwashed with water, acetonitrile, and ether
  10. customdried

Sources & evidence

ORD record
ord-4b7cefbb0b894fd8bf704186ec54342c
Source dataset
uspto-grants-1982_02
Patent number
US04315014

Reaction notes

Loading…