Lithium borohydride → HCID 21866249, compound

HRID 857789Notes

Reaction equation

HRID 857789 reaction equation
Cl[C:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=2[CH3:14])=[N:5][S:4][N:3]=1.[BH4-].[Li+]>C1COCC1>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]2[CH:2]=[N:3][S:4][N:5]=2)=[C:8]([CH3:14])[CH:9]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 21866306HCID 21866306, compound

Product 1

HCID 21866249HCID 21866249, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 3-chloro-4-(4-chloro-2-methylphenyl)-1,2,5-thiadiazole (0.503 g, 2.05 mmol) in THF (5.0 mL) was added 2 M lithium borohydride in THF (2.05 mL, 4.10 mmol). The reaction was stirred at ambient temperature for 15 min then was quenched with water and extracted into EtOAc. The organic phase was dried (Na2SO4) and reduced in vacuo. The residue was purified by flash chromatography (eluting with CH2Cl2/hexanes gradient, 1–15% CH2Cl2). 3-(4-Chloro-2-methylphenyl)-1,2,5-thiadiazole was isolated as a solid. 1H NMR (CDCl3, 400 MHz) δ 2.49 (s, 3H), 7.30 (d, J=8.2 Hz, 2H), 7.34 (s, 1H), 7.53 (d, J=8.2 Hz, 1H), 8.71 (s, 1H); MS m/z=211.4.

Workup

  1. customthen was quenched with water
  2. extractionextracted into EtOAc
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customThe residue was purified by flash chromatography (eluting with CH2Cl2/hexanes gradient, 1–15% CH2Cl2)

Sources & evidence

ORD record
ord-8361b420cddc4db6adfe733272c77706
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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