Acetic Acid → HCID 14099491, compound

HRID 1904165Notes

Reaction equation

HRID 1904165 reaction equation
[F:1][C:2]([F:23])([F:22])[O:3][C:4]1[CH:21]=[CH:20][C:7]2[N:8]=[C:9]([N:11]3[C:15](=[O:16])[C:14]([CH3:17])=[C:13]([CH3:18])[C:12]3=[O:19])[S:10][C:6]=2[CH:5]=1.[BH4-].[Na+].C(O)(=O)C>CO>[F:23][C:2]([F:1])([F:22])[O:3][C:4]1[CH:21]=[CH:20][C:7]2[N:8]=[C:9]([N:11]3[C:12](=[O:19])[C:13]([CH3:18])=[C:14]([CH3:17])[CH:15]3[OH:16])[S:10][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 14099490HCID 14099490, compound

Product 1

HCID 14099491HCID 14099491, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

N-(6-trifluoromethoxy-2-benzothiazolyl)-dimethylmaleimide (3.42 g) was added to methanol (150 ml), and sodium borohydride (0.19 g) was added at room temperature over 15 minutes. The mixture was further stirred for 3 hours. After the reaction, the reaction mixture was neutralized with acetic acid, and methanol was evaporated under reduced pressure. The residue was mixed with water and extracted with chloroform. Chloroform extracts were combined, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The solid residue was washed with a small amount of diethyl ether to give the desired N-(6-trifluoromethoxy-2-benzothiazolyl)-3,4-dimethyl-2-hydroxy-5-oxo-2,5-dihydropyrrole (3.05 g). m.p. 228°-231° C. ##STR13##

Workup

  1. additionwas added at room temperature over 15 minutes
  2. customAfter the reaction
  3. customwas evaporated under reduced pressure
  4. additionThe residue was mixed with water
  5. extractionextracted with chloroform
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. washThe solid residue was washed with a small amount of diethyl ether

Sources & evidence

ORD record
ord-4022a8dbedbf4af19fc172e6861462b8
Source dataset
uspto-grants-1989_06
Patent number
US04836844

Reaction notes

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