Isobutylamine → HCID 19907215, compound

HRID 2371425Notes

Reaction equation

HRID 2371425 reaction equation
C1(C)C(S([Cl:10])(=O)=O)=CC=CC=1.O[CH2:13][CH2:14][CH:15]1[S:20](=[O:22])(=[O:21])[C:19]2[S:23][C:24]([S:26](=[O:29])(=[O:28])[NH2:27])=[CH:25][C:18]=2[NH:17][CH2:16]1.[CH2:30]([NH2:34])[CH:31]([CH3:33])[CH3:32]>N1C=CC=CC=1>[ClH:10].[CH2:30]([NH:34][CH2:13][CH2:14][CH:15]1[S:20](=[O:22])(=[O:21])[C:19]2[S:23][C:24]([S:26](=[O:29])(=[O:28])[NH2:27])=[CH:25][C:18]=2[NH:17][CH2:16]1)[CH:31]([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 6558IsobutylamineHCID 8623o-Toluenesulfonyl chlorideHCID 10335685HCID 10335685, compound

Product 1

HCID 19907215HCID 19907215, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

Toluenesulfonyl chloride (1.91 g, 10 mmol) was added portionwise over 50 minutes to a cold (-10° C. to -5° C.) solution of 3-(2-hydroxyethyl)-2,3-dihydro-4,4-dioxo-6-sulfamoyl-1H-thieno[2,3-b][1,4]thiazine (1.56 g, 5 mmol) in pyridine (10 ml). This solution was stirred for about 0.5 hr as the temperature rose to 0° C., then isobutylamine (10 ml) was added. The resulting solution was heated at 100° C. overnight. The reaction mixture was concentrated to dryness, and the residue was treated with chloroform. The resulting white solid, 1.7 g, was dissolved in a minimum amount of water, the pH was adjusted to 7.5 and the solution was extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. After removal of the dried solvent, the residue was dissolved in ethanol and treated with excess ethanolic hydrogen chloride. Ether was added to the cloud point and the mixture aged for 18 hours. The resulting solid was collected and dried to yield 1.2 g 3-(2-isobutylaminoethyl)-2,3-dihydro-4,4-dioxo-6-sulfamoyl-1H-thieno[2,3-b][1,4]thiazine hydrochloride, mp 263°-265° C.

Workup

  1. customrose to 0° C.
  2. concentrationThe reaction mixture was concentrated to dryness
  3. additionthe residue was treated with chloroform
  4. dissolutionThe resulting white solid, 1.7 g, was dissolved in a minimum amount of water
  5. extractionthe solution was extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. customAfter removal of the dried solvent
  9. dissolutionthe residue was dissolved in ethanol
  10. additiontreated with excess ethanolic hydrogen chloride
  11. additionEther was added to the cloud point
  12. waitthe mixture aged for 18 hours
  13. customThe resulting solid was collected
  14. customdried

Sources & evidence

ORD record
ord-20917178097746739c7e5802894e8391
Source dataset
uspto-grants-1992_03
Patent number
US05093332

Reaction notes

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