2,6-Dichloroaniline → N-(2,6-Dichlorophenyl)-4,6-dimethyl-2-pyrimidinesulfonamide

HRID 34251

Reaction equation

HRID 34251 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH2:4].C([Li])CCC.[CH3:15][C:16]1[CH:21]=[C:20]([CH3:22])[N:19]=[C:18]([S:23](F)(=[O:25])=[O:24])[N:17]=1>C(COC)OC>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH:4][S:23]([C:18]1[N:17]=[C:16]([CH3:15])[CH:21]=[C:20]([CH3:22])[N:19]=1)(=[O:24])=[O:25]

Participants

5

Reactant 3

HCID 118462,6-DichloroanilineHCID 144047184,6-Dimethylpyrimidine-2-sulfonyl fluorideHCID 178418339Butyllithium

Product 1

HCID 14404703N-(2,6-Dichlorophenyl)-4,6-dimethyl-2-pyrimidinesulfonamide

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 2,6-dichloroaniline (1.0 g, 6.2 mmol) in dimethoxyethane (25 mL) was added butyl lithium (3.9 mL, 6.24 mmol). After 15 minutes, the solution was cooled to -30° and 4,6-dimethyl-2-pyrimidinesulfonyl fluoride (1.18 g, 6.2 mmol) was added. The mixture stirred for 12 hours with warming to 25° C. The mixture was concentrated and the residue was treated with 1N NaOH (2 mL) and extracted with ethyl acetate. The aqueous layer was acidified with 1N HCl and a solid was collected, m.p. 261°-263° C. NMR (90 MHZ) D6 -Acetone: δ 7.5 (m, 4H) and 2.5 (s, 6H).

Workup

  1. temperaturethe solution was cooled to -30°
  2. concentrationThe mixture was concentrated
  3. additionthe residue was treated with 1N NaOH (2 mL)
  4. extractionextracted with ethyl acetate
  5. customa solid was collected

Sources & evidence

ORD record
ord-061d9e615cca49ce98de4c0c3e9e94e9
Source dataset
uspto-grants-1988_08
Patent number
US04761173

Linked notes

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