Water → HCID 69443901, compound

HRID 446170Notes

Reaction equation

HRID 446170 reaction equation
[O:1]=[S:2]1(=[O:27])[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([CH2:12][N:13](C3C=CC=CC=3C#N)[N:14]3[CH:18]=[CH:17][N:16]=[CH:15]3)[CH:10]=[CH:11][C:4]=2[O:3]1.[BH4-].[Na+].[NH4+:30].[Cl-].O>CO>[O:1]=[S:2]1(=[O:27])[NH:7][CH2:6][C:5]2[CH:8]=[C:9]([CH2:12][N:13]([C:10]3[CH:9]=[CH:8][C:5]([C:6]#[N:30])=[CH:4][CH:11]=3)[N:14]3[CH:18]=[CH:17][N:16]=[CH:15]3)[CH:10]=[CH:11][C:4]=2[O:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 69445287HCID 69445287, compound

Product 1

HCID 69443901HCID 69443901, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of +[N-[(2,2-dioxido-1,2,3-benzoxathiazin-6-yl)methyl]-N-(1H-imidazol-1-yl)amino]benzonitrile (0.40 g, 1.05 mmol) in methanol (8 ml) was added portionwise NaBH4 (0.08 g, 2.11 mmol) and the reaction mixture was stirred at room temperature for 3 h. After addition of a saturated solution of NH4Cl (3 ml) and water (40 ml), the precipitate obtained was filtered, washed with water and dried to give a white solid. Crystallization from ethyl acetate with ethanol yielded the expected product (0.40 g, 82%, mp: 190° C.).

Workup

  1. customthe precipitate obtained
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried
  5. customto give a white solid
  6. customCrystallization from ethyl acetate with ethanol

Sources & evidence

ORD record
ord-bc021b7597004f48881437e52ce174f2
Source dataset
uspto-grants-2013_07
Patent number
US08476455B2

Reaction notes

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