Sulfuric Acid → HCID 20367582, compound

HRID 616506Notes

Reaction equation

HRID 616506 reaction equation
[CH3:1][NH:2][C:3]([NH:5][C:6]1[S:10][N:9]=[C:8]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:7]=1[C:16]#[N:17])=[O:4].S(=O)(=O)(O)[OH:19].C(=O)(O)[O-].[Na+]>>[CH3:1][NH:2][C:3]([NH:5][C:6]1[S:10][N:9]=[C:8]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:7]=1[C:16](=[O:19])[NH2:17])=[O:4]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 20367570HCID 20367570, compound

Product 1

HCID 20367582HCID 20367582, compound

Procedure

A stirred mixture of 10.5 g of 1-methyl-3-(4-cyano-3-(1-pyrrolidinyl)-5-isothiazolyl)urea and 15 ml of sulfuric acid was heated at 100° during 21/2 hours. The mixture was poured into 250 ml of stirred ice-water and neutralized by slow addition of saturated sodium bicarbonate solution. The separated solid was collected by filtration. The filtrate was allowed to stand for a short time, and filtered again. The collected solid was found to be a mixture of the desired product and unreacted starting material. A third solid that formed when the filtrate was allowed to stand overnight was isolated by filtration to give 4.6 g of 1-methyl-3-(4-carbamoyl-3-(1-pyrrolidinyl)-5-isothiazolyl)urea, which darkened at 241°, then decomposed at 257°. The nmr spectrum was consistent with the assigned structure.

Workup

  1. temperaturewas heated at 100° during 21/2 hours
  2. filtrationThe separated solid was collected by filtration
  3. filtrationfiltered again
  4. additiona mixture of the desired product
  5. customA third solid that formed when the filtrate
  6. customwas isolated by filtration

Sources & evidence

ORD record
ord-7250de83ca704129aa823dba1e5237b6
Source dataset
uspto-grants-1978_02
Patent number
US04075001

Reaction notes

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