Triethylamine → N-[4-(5-chloro-2-pyrimidinyloxy)-3-methylphenyl]-2-nitrobenzenesulfenamide

HRID 704317Notes

Reaction equation

HRID 704317 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][C:10]=2[CH3:16])=[N:6][CH:7]=1.C(N(CC)CC)C.[N+:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33]Cl)([O-:26])=[O:25].C(OCC)(=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[N:6][C:5]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH:13][S:33][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[N+:24]([O-:26])=[O:25])=[CH:11][C:10]=2[CH3:16])=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 243192-Nitrobenzenesulfenyl chlorideHCID 142078084-((5-Chloropyrimidin-2-yl)oxy)-3-methylaniline

Product 1

HCID 10000368N-[4-(5-chloro-2-pyrimidinyloxy)-3-methylphenyl]-2-nitrobenzenesulfenamideYield 83.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2.0 g of 4-(5 chloro-2-pyrimidinyloxy)-3methylaniline and 0.94 g of triethylamine were dissolved in 20 ml of toluene, and a solution of 1.61 g of 2-nitrobenzenesulfenyl chloride dissolved in 5 ml of toluene was dropwise added thereto at room temperature. The mixture was reacted at room temperature for 1 hour under stirring. After completion of the reaction, ethyl acetate was added to the reaction product, and the ethyl acetate layer was washed with water, dried over Glauber's salt and then purified by column chromatography to obtain 2.76 g of N-[4-(5-chloro-2-pyrimidinyloxy)-3-methylphenyl]-2-nitrobenzenesulfenamide (Intermediate Compound No. 37) (melting point: 74°-85° C.) in a yellow non-crystalline form.

Workup

  1. additionwas dropwise added
  2. customat room temperature
  3. customThe mixture was reacted at room temperature for 1 hour
  4. additionwas added to the reaction product
  5. washthe ethyl acetate layer was washed with water
  6. dry with materialdried over Glauber's salt
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-635377d9a71e459093799c5dc60a7731
Source dataset
uspto-grants-1991_01
Patent number
US04987135

Reaction notes

Loading…