Thionyl Chloride → N-[3-(2-Chloro-5-cyano-pyrimidin-4-ylamino)-propyl]-3-nitro-benzenesulfonamide

HRID 970426Notes

Reaction equation

HRID 970426 reaction equation
C([NH:5][C:6]([C:8]1[C:9]([NH:15][CH2:16][CH2:17][CH2:18][NH:19][S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=2)(=[O:22])=[O:21])=[N:10][C:11]([Cl:14])=[N:12][CH:13]=1)=O)(C)(C)C.S(Cl)(Cl)=O>>[Cl:14][C:11]1[N:10]=[C:9]([NH:15][CH2:16][CH2:17][CH2:18][NH:19][S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=2)(=[O:22])=[O:21])[C:8]([C:6]#[N:5])=[CH:13][N:12]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 590203532-Chloro-4-[3-(3-nitro-benzenesulfonylamino)-propylamino]-pyrimidine-5-carboxylic acid-tert-butylamide

Product 1

HCID 17986386N-[3-(2-Chloro-5-cyano-pyrimidin-4-ylamino)-propyl]-3-nitro-benzenesulfonamide

Procedure

125 mg (0.27 mmol) of 2-chloro-4-[3-(3-nitro-benzenesulfonylamino)-propylamino]-pyrimidine-5-carboxylic acid-tert-butylamide is mixed with 4 ml of thionyl chloride and stirred under reflux for 19 hours. The reaction mixture is concentrated by evaporation. It is mixed with water and toluene and evaporated to the dry state in a rotary evaporator. 110 mg (0.27 mmol, corresponding to 100% of theory) of the product is obtained.

Workup

  1. temperatureunder reflux for 19 hours
  2. concentrationThe reaction mixture is concentrated by evaporation
  3. additionIt is mixed with water and toluene
  4. customevaporated to the dry state in a rotary evaporator
  5. custom110 mg (0.27 mmol, corresponding to 100% of theory) of the product is obtained

Sources & evidence

ORD record
ord-30a5150905ec4b3c82a020500f0c0748
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

Loading…