Hydrochloric Acid → HCID 54684925, compound

HRID 2164112Notes

Reaction equation

HRID 2164112 reaction equation
[CH3:1][N:2]1[CH2:15][C:14](=[O:16])[C:5]2[N:6]([CH3:13])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:4]=2[S:3]1(=[O:18])=[O:17].[C:19]1([N:25]=[C:26]=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[H-].[Na+].Cl>CN(C)C=O>[CH3:1][N:2]1[C:15]([C:26]([NH:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:27])=[C:14]([OH:16])[C:5]2[N:6]([CH3:13])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:4]=2[S:3]1(=[O:18])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7672Phenyl isocyanateHCID 24758Sodium hydrideHCID 22750003HCID 22750003, compound

Product 1

HCID 54684925HCID 54684925, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1.0 gm (3.7 millimols) of 2,5-dihydro-2,5-dimethyl-1,2-thiazino[5,6-b]indole-4(3H)-one-1,1-dioxide and 0.44 ml (4.0 millimols) of phenyl isocyanate in 20 ml of dimethylformamide was added to a suspension of 230 mgm of a 55% sodium hydride-in-oil dispersion (5.0 millimols) in 15 ml of dimethylformamide, while cooling on ice. The reaction mixture was stirred for 30 min. on an ice bath and then for 4 hours at room temperature. Afterwards, it was stirred into 100 ml of aqueous 3 N hydrochloric acid. The precipitate formed thereby was filtered off, washed with water, dried and recrystallized from xylene, yielding 340 mgm (27% of theory) of 2,5-dihydro-2,5-dimethyl-4-hydroxy-N-phenyl-1,2-thiazino[5,6-b]indole-3-carboxamide-1,1-dioxide; M.p.: 269°-270° C. (decomposition).

Workup

  1. temperaturewhile cooling on ice
  2. waitfor 4 hours at room temperature
  3. customThe precipitate formed
  4. filtrationthereby was filtered off
  5. washwashed with water
  6. customdried
  7. customrecrystallized from xylene

Sources & evidence

ORD record
ord-42a7aa5780584c38bfc302097337fc33
Source dataset
uspto-grants-1979_01
Patent number
US04137313

Reaction notes

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