Water → (5-Fluoro-2-(methylthio)benzo[d]thiazol-6-yl)methanamine

HRID 1848179Notes

Reaction equation

HRID 1848179 reaction equation
[F:1][C:2]1[C:3]([C:13]#[N:14])=[CH:4][C:5]2[S:9][C:8]([S:10][CH3:11])=[N:7][C:6]=2[CH:12]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[F:1][C:2]1[C:3]([CH2:13][NH2:14])=[CH:4][C:5]2[S:9][C:8]([S:10][CH3:11])=[N:7][C:6]=2[CH:12]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 866811685-Fluoro-2-(methylthio)benzo[d]thiazole-6-carbonitrile

Product 1

HCID 86681148(5-Fluoro-2-(methylthio)benzo[d]thiazol-6-yl)methanamineYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 5-fluoro-2-(methylthio)benzo[d]thiazole-6-carbonitrile in anhydrous THF (20 mL) at −20° C. under argon was added dropwise lithium aluminum hydride (2 M solution in THF, 11.7 mL, 5.9 mmol). After 1 h, water (500 μL) and 1 M aq NaOH (500 μL) were added slowly to the reaction mixture. After 5 minutes, additional water (2 mL) was added and the mixture was stirred at rt for 30 minutes. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 5% MeOH in CH2Cl2 to afford (5-fluoro-2-(methylthio)benzo[d]thiazol-6-yl)methanamine (128 mg, 29%) as a colorless oil. 1H NMR (500 MHz, DMSO-d6) δ 8.07 (d, J=7.1 Hz, 1H), 7.64 (d, J=11.1 Hz, 1H), 3.83 (s, 2H), 2.78 (s, 3H), 1.80-2.06 (m, 2H); LCMS (ESI) m/z 229 (M+H)+.

Workup

  1. waitAfter 5 minutes
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel flash chromatography
  5. washeluting with 5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-dc9a5e707c764ce8ab111613a0577696
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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