Tetrahydrofuran → HCID 57855982, compound

HRID 2039626Notes

Reaction equation

HRID 2039626 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([S:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])=[C:6]([Cl:20])[C:5]=1SCC[Si](C)(C)C.[NH4+:29].[Cl-].C1COCC1>CCO.CO.[Zn]>[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([S:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])=[C:6]([Cl:20])[C:5]=1[NH2:29]

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 25517Ammonium Chloride2×HCID 86633753HCID 86633753, compound

Product 1

HCID 57855982HCID 57855982, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

3-chloro-5-nitro-2,4-bis-(2-trimethylsilanyl-ethylsulfanyl)-benzoic acid methyl ester) in a ratio 74:36 (NMR integrals), are suspended in 16 ml of EtOH and 20 ml of MeOH. Then, 16 ml of a saturated NH4Cl aqueous solution are added followed by 20 ml of THF. 788 mg (0.012 mol, 4.4 eq.) of dust powdered zinc are added and the reaction is stirred during 1 h 30. 50 ml of a saturated NH4Cl aqueous solution are added to the mixture and the product is extracted with CH2Cl2 (3 times). The regrouped organic phases are dried with Na2SO4, filtered and evaporated. A column chromatography purification on silica gel with hexanes and EtOAc gave 680 mg (78%) of pure 2,5-diamino-3-chloro-4-(2-trimethylsilanyl-ethylsulfanyl)-benzoic acid methyl ester; 1H-NMR (CDCl3, 300 MHz): 0.02 (s, 9H), 0.78-0.89 (m, 2H), 2.83-2.91 (m, 2H), 3.88 (s, 3H), 7.33 (d, 1H) ppm.

Workup

  1. additionare added
  2. extractionthe product is extracted with CH2Cl2 (3 times)
  3. dry with materialThe regrouped organic phases are dried with Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customA column chromatography purification on silica gel with hexanes and EtOAc

Sources & evidence

ORD record
ord-51934db60e6c4966b2decb1826183acc
Source dataset
uspto-grants-2013_11
Patent number
US08580785B2

Reaction notes

Loading…