Water → N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1,2-benzenedisulfonamide

HRID 2232017Notes

Reaction equation

HRID 2232017 reaction equation
[C:1]1([S:11]([NH2:14])(=[O:13])=[O:12])[C:2]([S:7]([NH2:10])(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.C[Al](C)C.C[O:20][C:21](=O)[NH:22][C:23]1[N:28]=[C:27]([O:29][CH3:30])[CH:26]=[C:25]([O:31][CH3:32])[N:24]=1.O>C(Cl)Cl.Cl.C(O)(=O)C>[CH3:30][O:29][C:27]1[CH:26]=[C:25]([O:31][CH3:32])[N:24]=[C:23]([NH:22][C:21]([NH:10][S:7]([C:2]2[C:1]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:6][CH:5]=[CH:4][CH:3]=2)(=[O:9])=[O:8])=[O:20])[N:28]=1

Participants

8

Reactant 4

HCID 962WaterHCID 13314628Methyl (4,6-dimethoxypyrimidin-2-yl)carbamateHCID 13885364Benzene-1,2-disulfonamideHCID 16682925Trimethylaluminum

Product 1

HCID 13885365N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1,2-benzenedisulfonamideYield 17%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 0.7 g of 1,2-benzenedisulfonamide and 1.5 ml of trimethylaluminum in 70 ml of anhydrous methylene chloride was added 0.6 g of 4,6-dimethoxypyrimidin-2-ylcarbamic acid methyl ester under N2 with stirring. After addition, the mixture was stirred at room temperature for 30 minutes and was then heated to reflux for 12 hours. The reaction mixture was then cooled down to room temperature. To this mixture was added 50 ml of methylene chloride, 100 ml of water, 10 ml of acetic acid and 5 drops of concentrated hydrochloric acid. The mixture was then stirred at room temperature for 20 minutes and was filtered. The organic layer was then separated, washed with water, dried over sodium sulfate and concentrated. The residue was then chromatographed on silica gel (CH2Cl2 /acetic acid 1:1) to yield 0.2 g of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1,2-benzenedisulfonamide, m.p. 192°-193° C.

Workup

  1. additionAfter addition
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. temperaturewas then heated
  4. temperatureto reflux for 12 hours
  5. stirringThe mixture was then stirred at room temperature for 20 minutes
  6. filtrationwas filtered
  7. customThe organic layer was then separated
  8. washwashed with water
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated
  11. customThe residue was then chromatographed on silica gel (CH2Cl2 /acetic acid 1:1)

Sources & evidence

ORD record
ord-1a7e31a84a8f4450b025d6221115b600
Source dataset
uspto-grants-1988_11
Patent number
US04786316

Reaction notes

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