Sodium sulfate decahydrate → HCID 58962955, compound

HRID 917557Notes

Reaction equation

HRID 917557 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:14])[C:9]=1[NH:10][CH2:11][CH2:12][CH3:13])[C:5]#[N:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:14])[C:9]=1[NH:10][CH2:11][CH2:12][CH3:13])[CH2:5][NH2:6]

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 58962998HCID 58962998, compound

Product 1

HCID 58962955HCID 58962955, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step AR3. To crude 3-chloro-5-bromo-4-(propylamino)-benzonitrile (450 mg, 1.65 mg) in dry THF (15 mL) was added lithium aluminum hydride (200 mg, 5.3 mmol) in portion. After stirred at RT for 3 hours, sodium sulfate decahydrate (1.7 g, 5.3 mmol) was added in portion and the mixture was stirred for 30 minutes. The solid was filtered off and the filtration was added to a silicon gel column and trapped there for 24 hours. Flash chromatography with DCM, then 20% MeOH in DCM, then 50% MeOH in DCM gave 3-chloro-5-bromo-4-(propylamino)-benzylamine (121 mg, 26.4%). 1H NMR (CD3OD): δ 1.04 (t, 3H), 1.66 (m, 2H), 3.34 (t, 2H), 3.80 (s, 3H), 7.43 (s, 1H), 7.57 (s, 1H).

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. filtrationThe solid was filtered off
  3. filtrationthe filtration
  4. additionwas added to a silicon gel column
  5. waittrapped there for 24 hours

Sources & evidence

ORD record
ord-af51d38d2c02471fb2f78b3f9b5c21fb
Source dataset
uspto-grants-2007_09
Patent number
US07273882B2

Reaction notes

Loading…