Diethylammonium chloride → HCID 21934525, compound

HRID 1241439Notes

Reaction equation

HRID 1241439 reaction equation
[N:1]1[C:10]2[NH:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][C:13]#[N:14].O.[SH2:16].[Na].Cl.C(NCC)C>CN(C=O)C.O>[N:1]1[C:10]2[NH:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][C:13](=[S:16])[NH2:14]

Participants

6

Reactant 3

HCID 10197650Diethylammonium chlorideHCID 21934515HCID 21934515, compoundHCID 53442613Sodium hydrogen sulfide hydrate

Product 1

HCID 21934525HCID 21934525, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

Reagents 3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propanenitrile (100 mg), sodium hydrogen sulfide hydrate (360 mg), diethylamine hydrochloride (530 mg) were mixed in DMF (10 mL). The mixture was warmed to 55° C. and stirred at this temperature for about 24 h. The mixture was allowed to cool and then diluted with water (30 mL) followed by extraction with ethyl acetate (3×25 mL). The extracts were combined and washed with water (3×20 mL). The organic phase was dried (magnesium sulfate) and filtered. The solution was concentrated and column purification (CHCl3: MeOH=10:1) to yield a yellow solid 101 mg (89%). 1H NMR (DMSO-d6) δ 9.30 (d, 2H), 7.10 (d, 2H), 6.35 (m, 2H), 3.25 (m, 2H), 2.80 (m, 2H), 2.75 (m, 2H), 2.64 (m, 2H), 1.72 (m, 2H).

Workup

  1. temperatureto cool
  2. extractionfollowed by extraction with ethyl acetate (3×25 mL)
  3. washwashed with water (3×20 mL)
  4. dry with materialThe organic phase was dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationThe solution was concentrated
  7. customcolumn purification (CHCl3: MeOH=10:1)

Sources & evidence

ORD record
ord-98521497fb3a4c15b51579adc052e3dc
Source dataset
uspto-grants-2006_10
Patent number
US07115596B2

Reaction notes

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