Chloroform → HCID 18539786, compound

HRID 411114Notes

Reaction equation

HRID 411114 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=[CH:13][N+:14]([O-:16])=[O:15])=[C:10]([CH:17]=[S:18](=[O:20])=[O:19])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(Cl)(Cl)Cl.[BH4-].[Na+]>CC(O)C>[Cl:1][C:2]1[C:11]([CH2:12][CH2:13][N+:14]([O-:16])=[O:15])=[C:10]([CH:17]=[S:18](=[O:20])=[O:19])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 88103065HCID 88103065, compound

Product 1

HCID 18539786HCID 18539786, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

19.4 g (61 mmol) of methyl 2-chloro-3-(2-nitroethenyl)-4-sulfonylmethylbenzoate and 121 g of silica gel 60 are suspended in 180 ml of 2-propanol and 970 ml of chloroform and treated at room temperature with 3.5 g (94 mmol) of sodium borohydride. The reaction mixture is filtered, the filtrate is washed with dichloromethane/methanol 1:1 (v/v) and the organic phase is freed from the solvent under reduced pressure. Yield: 19.5 g; 1H NMR, δ [ppm], CDCl3; 3.2 (s), 3.9 (m), 4.0 (s), 4.7 (m), 7.8 (d), 8.1 (d).

Workup

  1. filtrationThe reaction mixture is filtered
  2. washthe filtrate is washed with dichloromethane/methanol 1:1 (v/v)

Sources & evidence

ORD record
ord-b9e31ce5163b4f76981354cf75d389f1
Source dataset
uspto-grants-2003_05
Patent number
US06559100B1

Reaction notes

Loading…