Methanol → 3-fluoro-4-[tetrahydro-1,1-dioxido-2-(2-propenyl)-2H-1,2-thiazin-4-yl]benzenamine

HRID 2229138Notes

Reaction equation

HRID 2229138 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH:11]1[CH2:16][CH2:15][S:14](=[O:18])(=[O:17])[N:13]([CH2:19][CH:20]=[CH2:21])[CH2:12]1.[BH4-].[Na+].CO.[Cl-].[NH4+]>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH:11]1[CH2:16][CH2:15][S:14](=[O:18])(=[O:17])[N:13]([CH2:19][CH:20]=[CH2:21])[CH2:12]1

Participants

6

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 183691474-(2-fluoro-4-nitrophenyl)tetrahydro-2-(2-propenyl)-2H-1,2-thiazine 1,1-dioxide

Product 1

HCID 220912753-fluoro-4-[tetrahydro-1,1-dioxido-2-(2-propenyl)-2H-1,2-thiazin-4-yl]benzenamineYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(2-Fluoro-4-nitrophenyl)tetrahydro-2-(2-propenyl)-2H-1,2-thiazine 1,1-dioxide (1.303 g, 4.15 mmol) and cuprous bromide: dimethyl sulfide complex (0.855 g, 4.15 mmol) are stirred at ice temperature in dry THF (30 ml). Sodium borohydride (1.25 g, 33.07 mmol) is added and the mixture stirred for 20 min. Methanol (10 ml) is carefully added over 30 min followed by ammonium chloride solution (50 ml). The mixture is extracted with methylene chloride (2×100 ml), washed with water (50 ml) and brine (50 ml), dried (MgSO4) and evaporated to yield the product as a cream solid (1.178 g, 100%) mp 96°.

Workup

  1. extractionThe mixture is extracted with methylene chloride (2×100 ml)
  2. washwashed with water (50 ml) and brine (50 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-dc030c604e854d3ba7fb1f91a0c03a9b
Source dataset
uspto-grants-2002_07
Patent number
US06420360B1

Reaction notes

Loading…