Water → HCID 68505446, compound

HRID 220212Notes

Reaction equation

HRID 220212 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[C:9]2[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:10]=2[S:11][C:12]=1[CH:13]([O:19][CH3:20])[CH:14]([N+:16]([O-])=O)[CH3:15].O>C(OCC)C>[Cl:7][C:8]1[C:9]2[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:10]=2[S:11][C:12]=1[CH:13]([O:19][CH3:20])[CH:14]([NH2:16])[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 59479543HCID 59479543, compound

Product 1

HCID 68505446HCID 68505446, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In a sulfonation flask 15 ml (0.015 mol) of an etheral 1 molar LiAlH4 solution is diluted with 40 ml of diethylether. A solution of 0.97 g (0.003 mol) 3,5-dichloro-2-(1-methoxy-2-nitropropyl)benzo[b]thiophene and 30 ml diethylether is added under stirring in such a manner that the internal temperature remains constant at 0-5° C. Then the mixture is warmed up to it and stirring continued for 5 h. Then the reaction mixture is cooled again and water added slowly. After quenching sodium sulphate is added. Filtration and distilling off the solvent in a water jet vacuum, the raw material is obtained. Purification is achieved by column chromatography (eluent: tert. butylmethylether/EtOH 3:1). Yield: 0.62 g (87% of theory) yellowish oil consisting of a diastereoisomeric mixture (ratio:ca. 2:1). 1H-NMR: 1.05/d/3H-DS1 (minor isomer), 1.13/d/3H, DS2 (major isomer), 3.2/m/1H-DS1, 3.35/s/6H-DS1+DS2, 3.39/m/1H-DS2, 4.45/d/1H-DS1, 4.52/d/1H-DS2, 7.38/m/2H-DS1+DS2, 7.72/d/2H-DS1+DS2, 7.8/2 s/DS1+DS2.

Workup

  1. customremains constant at 0-5° C
  2. temperatureThen the mixture is warmed up to it
  3. stirringstirring
  4. temperatureThen the reaction mixture is cooled again
  5. customAfter quenching sodium sulphate
  6. additionis added
  7. filtrationFiltration
  8. distillationdistilling off the solvent in a water jet vacuum

Sources & evidence

ORD record
ord-141e67acb4fb4df884f6c581beec1344
Source dataset
uspto-grants-2012_06
Patent number
US08202894B2

Reaction notes

Loading…