Sodium hydride → HCID 18916416, compound

HRID 1290644Notes

Reaction equation

HRID 1290644 reaction equation
[H-].[Na+].[C:3]([NH:6][C:7]1[O:8][C:9]2[C:15]([N:16]3[C:21](=[O:22])[CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[N:18]([CH3:27])[C:17]3=[O:28])=[C:14]([F:29])[CH:13]=[C:12]([Cl:30])[C:10]=2[N:11]=1)(=[O:5])[CH3:4].[CH3:31][S:32](Cl)(=[O:34])=[O:33]>O1CCCC1>[C:3]([N:6]([C:7]1[O:8][C:9]2[C:15]([N:16]3[C:21](=[O:22])[CH:20]=[C:19]([C:23]([F:25])([F:24])[F:26])[N:18]([CH3:27])[C:17]3=[O:28])=[C:14]([F:29])[CH:13]=[C:12]([Cl:30])[C:10]=2[N:11]=1)[S:32]([CH3:31])(=[O:34])=[O:33])(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 18916382HCID 18916382, compound

Product 1

HCID 18916416HCID 18916416, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred suspension of 2.0 grams (51 mmole) of 60% sodium hydride (in mineral oil) in 25 mL of tetrahydrofuran is cooled in an ice bath. To this is added a solution of 10.2 grams (25.5 mmole) of 3-(2-acetylamino-4-chloro-6-fluorobenzoxazol-7-yl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)pyrimidinedione in 25 mL of tetrahydrofuran. Upon completion of the addition 2.9 grams (25.3 mmole) of methanesulfonyl chloride is added. The reaction mixture is heated to reflux, where it stirs for one hour and then concentrated under reduced pressure, yielding 3-[2-(N-acetyl-N-methylsulfonylamino)-4-chloro-6-fluorobenzoxazol-7-yl]-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione.

Workup

  1. temperatureis cooled in an ice bath
  2. additionis added
  3. temperatureThe reaction mixture is heated
  4. temperatureto reflux
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9174589327f14271a75a845cb4e3ceaa
Source dataset
uspto-grants-1998_05
Patent number
US05753595

Reaction notes

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