1-Chloro-2,6-dinitrobenzene → HCID 53919988, compound

HRID 1459664Notes

Reaction equation

HRID 1459664 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[SH:9].Cl[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][C:12]=1[N+]([O-])=O.C(N(CC)C(C)C)(C)C.[Cl-].[NH4+]>CN(C)C=O>[F:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[NH:1][C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][C:12]=1[S:9]2

Participants

6

Reactant 4

HCID 118141-Chloro-2,6-dinitrobenzeneHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 3205472-Amino-5-fluorobenzene-1-thiol

Product 1

HCID 53919988HCID 53919988, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.2 g (15 mmol) of 2-amino-5-fluorobenzenethiol was dissolved in 30 ml of dimethylformamide and 2.5 g (12 mmol) of 1-chloro-2,6-dinitrobenzene was added thereto. The resulting mixture was stirred at room temperature. After 12 hours, 2.6 ml of N,N-diisopropylethylamine was added thereto and the mixture was heated at 80° C. for 2 hours. After cooling, the reaction mixture was poured into a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. After concentrating, the residue was purified by silica gel column chromatography. Thus 1.2 g of the title compound was obtained.

Workup

  1. temperaturethe mixture was heated at 80° C. for 2 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. concentrationAfter concentrating
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5cfac4f3dc584ce4a27d47cb60e98837
Source dataset
uspto-grants-1998_12
Patent number
US05854274

Reaction notes

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