Water → HCID 15766687, compound

HRID 1707567Notes

Reaction equation

HRID 1707567 reaction equation
[F:1][C:2]1[C:15]([N:16]2[C:21](=[O:22])[CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[NH:18][C:17]2=[O:27])=[CH:14][C:5]2[N:6]([CH:10]([CH2:12][CH3:13])[CH3:11])[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1.[H-].[Na+].[N+:30](C1C=C([N+]([O-])=O)C=CC=1ON)([O-])=O.O>CN(C)C=O>[F:1][C:2]1[C:15]([N:16]2[C:21](=[O:22])[CH:20]=[C:19]([C:23]([F:24])([F:25])[F:26])[N:18]([NH2:30])[C:17]2=[O:27])=[CH:14][C:5]2[N:6]([CH:10]([CH2:12][CH3:13])[CH3:11])[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 87140O-(2,4-dinitrophenyl)hydroxylamineHCID 15766686HCID 15766686, compound

Product 1

HCID 15766687HCID 15766687, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[6-fluoro-3-sec-butyl-2(3H)-benzothiazolon-5-yl]-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dione (2.0 g) in dimethylformamide (10 g), sodium hydride (0.3 g) and 2,4-dinitrophenoxyamine (1.8 g) were added, and the resultant mixture was heated at 40 to 60° C. for 3 hours. After completion of the reaction, the reaction mixture was poured into water, extracted with ethyl acetate and concentrated. The residue was purified by silica gel column chromatography to give 1-[6-fluoro-3-sec-butyl-2(3H)-benzothiazolon-5-yl]-3-amino-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dione (0.4 g).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7c1a0fdeb8484b648c0f2d73bce27ddb
Source dataset
uspto-grants-1994_10
Patent number
US05354730

Reaction notes

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