Triethylamine → HCID 14747831, compound

HRID 35425Notes

Reaction equation

HRID 35425 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([OH:14])=[CH:9][C:8]=1[N:15]1[C:20](=[O:21])[N:19]([CH3:22])[C:18](=[O:23])[CH:17]=[N:16]1.C(N(CC)CC)C>O1CCCC1.O>[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([O:14][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:9][C:8]=1[N:15]1[C:20](=[O:21])[N:19]([CH3:22])[C:18](=[O:23])[CH:17]=[N:16]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 142769422-(2,4-dichloro-5-hydroxyphenyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione2×

Product 1

HCID 14747831HCID 14747831, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.35 g (0.0031 mole) of methanesulfonyl chloride in 5 mL of tetrahydrofuran was added to a stirred solution of 0.8 g (0.0028 mole) of 2-(2,4-dichloro-5-hydroxyphenyl)-4-methyl-1,2,4-triazine-3,5-(2H,4H)-dione (Compound 9, Example III H) and 0.30 g (0.0031 mole) of triethylamine in 10 mL of tetrahydrofuran. The reaction mixture was stirred at room temperature for approximately 18 hours, then diluted with water. The resultant mixture was extracted with ethyl acetate, and the extract was dried over anhydrous magnesium sulfate. The dried extract was filtered, and the filtrate was evaporated under reduced pressure to give 0.81 g of 2-(2,4-dichloro-5-methylsulfonyloxyphenyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione as a solid, Compound 23 in the tables.

Workup

  1. extractionThe resultant mixture was extracted with ethyl acetate
  2. dry with materialthe extract was dried over anhydrous magnesium sulfate
  3. extractionThe dried extract
  4. filtrationwas filtered
  5. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-635c8c3058544490a26eb4b679e5c00b
Source dataset
uspto-grants-1988_08
Patent number
US04766233

Reaction notes

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