Sodium hydride → HCID 68642107, compound

HRID 1498966Notes

Reaction equation

HRID 1498966 reaction equation
[H-].[Na+].[NH:3]1[CH2:8][CH2:7][S:6][CH2:5][C:4]1=[O:9].F[C:11]1[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][C:12]=1[N+:22]([O-:24])=[O:23]>O1CCCC1>[N+:22]([C:12]1[CH:13]=[C:14]([CH:20]=[CH:21][C:11]=1[N:3]1[CH2:8][CH2:7][S:6][CH2:5][C:4]1=[O:9])[C:15]([O:17][CH2:18][CH3:19])=[O:16])([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 884021,4-Tetrahydrothiazine-3-oneHCID 21277355Ethyl 4-fluoro-3-nitrobenzoate

Product 1

HCID 68642107HCID 68642107, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (60%, 171 mg, 4.27 mmol) was suspended in tetrahydrofuran (10 ml), and thiomorpholin-3-one (500 mg, 4.27 mmol) prepared in the Step 40-1-1 was added thereto. The mixture was stirred at a room temperature for 5 minutes, and a solution (10 ml) of ethyl 4-fluoro-3-nitrobenzoate (910 mg, 4.27 mmol) prepared in the Step 1-1-1 in tetrahydrofuran was slowly added to the mixture. The resulting mixture was stirred at a room temperature for 4 hours. The mixture was concentrated, and chloroform was added thereto. The resulting mixture was washed with a saturated sodium bicarbonate solution. The washed product was dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) and washed with methanol to give the title compound (360 mg, 27%) as a yellow powder.

Workup

  1. additionwas added
  2. additionwas slowly added to the mixture
  3. stirringThe resulting mixture was stirred at a room temperature for 4 hours
  4. concentrationThe mixture was concentrated
  5. additionchloroform was added
  6. washThe resulting mixture was washed with a saturated sodium bicarbonate solution
  7. dry with materialThe washed product was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)
  10. washwashed with methanol

Sources & evidence

ORD record
ord-a69ecc0c807d4e7897dc861368e29663
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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