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

HRID 970451Notes

Reaction equation

HRID 970451 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-cf3bb77c30804f6cb4508dd9303d2f94
Source dataset
uspto-grants-2007_12
Patent number
US07312226B2

Reaction notes

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