tert-Butanol → HCID 54696557, compound

HRID 2164095Notes

Reaction equation

HRID 2164095 reaction equation
[CH2:1]([N:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[S:12](=[O:22])(=[O:21])[N:13]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[C:14](=[O:15])[C:4]1=2)[CH3:2].C[O-].[Na+].C(O)(C)(C)C>C1(C)C=CC=CC=1>[CH2:1]([N:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[S:12](=[O:22])(=[O:21])[NH:13][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:14]([OH:15])[C:4]1=2)[CH3:2]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 10591910HCID 10591910, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 54696557HCID 54696557, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

19.3 gm (60 millimols) of methyl 4-ethyl-3,4-dihydro-3-oxo-2H-isothiazolo[4,5-b]indole-2-acetate-1,1-dioxide and a suspension of 9.7 gm (180 millimols) of sodium methylate in 150 ml of toluene were admixed, while vigorously stirring, with 30 ml of dry tert. butanol, and the mixture was stirred for 30 minutes at room temperature and then for 90 minutes at 60° C. Subsequently, the reaction mixture was cooled on an ice bath and admixed with 120 ml of ice water. The organic phase was extracted with water, and the aqueous phase was extracted with ether. The combined aqueous phases were then acidified with hydrochloric acid to pH 3. The precipitate formed thereby was washed with water, methanol and ether, and after recrystallization from ethylene chloride yielded 8.3 gm (43% of theory) of methyl 5-ethyl-2,5-dihydro-4-hydroxy-1,2-thiazino-[5,6-b]indole-3-carboxylate 1.1-dioxide; M.p.: 216° C. (decomposition).

Workup

  1. waitfor 90 minutes at 60° C
  2. temperatureSubsequently, the reaction mixture was cooled on an ice bath
  3. extractionThe organic phase was extracted with water
  4. extractionthe aqueous phase was extracted with ether
  5. customThe precipitate formed
  6. washthereby was washed with water, methanol and ether
  7. customafter recrystallization from ethylene chloride

Sources & evidence

ORD record
ord-1c0df20b1801478cb98ddb579b5f7128
Source dataset
uspto-grants-1979_01
Patent number
US04137313

Reaction notes

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