Sulfadiazine → N-Pyrimidin-2-yl-4-thioformylamino-benzenesulfonamide chloride

HRID 2052822Notes

Reaction equation

HRID 2052822 reaction equation
[CH:1]1[CH:2]=[N:3][C:4]([NH:7][S:8]([C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)(=[O:10])=[O:9])=[N:5][CH:6]=1.[C:18](Cl)([Cl:20])=[S:19].C(N(CC)CC)C>ClCCl>[Cl-:20].[N:3]1[CH:2]=[CH:1][CH:6]=[N:5][C:4]=1[NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][CH:18]=[S:19])=[CH:13][CH:12]=1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 5215SulfadiazineHCID 8471TriethylamineHCID 10040Thiophosgene

Product 1

HCID 86601004N-Pyrimidin-2-yl-4-thioformylamino-benzenesulfonamide chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of sulfadiazine (192 mg, 0.77 mmol) in dichloromethane (20 mL) were slowly added thiophosgene (0.06 mL, 0.83 mmol) and triethylamine (0.05 mL, 0.32 mmol) under cooling with an ice bath. After the reaction mixture was stirred for 5 hours at room temperature, it was washed with water and brine, dried over anhydrous sodium sulfate, filtered, evaporated and dried under vacuum; and the product was used immediately for the next reaction.

Workup

  1. temperatureunder cooling with an ice bath
  2. washit was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customdried under vacuum
  7. customand the product was used immediately for the next reaction

Sources & evidence

ORD record
ord-9e9d4e60190c45a9823e7929d50072f9
Source dataset
uspto-grants-2008_02
Patent number
US07326712B2

Reaction notes

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