Water → HCID 23458004, compound

HRID 1448604Notes

Reaction equation

HRID 1448604 reaction equation
[C:1]1([CH:6]=[N:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[S:5][CH:4]=[CH:3][CH:2]=1.[CH2:14]([Li])[CH2:15][CH2:16][CH3:17].O>CCOCC>[CH2:14]([CH:6]([NH:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)[C:1]1[S:5][CH:4]=[CH:3][CH:2]=1)[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 23458001HCID 23458001, compoundHCID 178418339Butyllithium

Product 1

HCID 23458004HCID 23458004, compoundYield 106.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a stirred, cooled (10°-20° C.) a solution of 3.77 grams of 4-(2-thenylideneamino)pyridine in 100 milliliters of dry ether, a solution containing 0.025 mole butyl lithium in 50 milliliters of dry ether was added dropwise. The resulting solution was stirred at room temperature for 4 hours, and then diluted with 150 ml dry ether before cautious addition of 50 ml. water. The organic phase was dried (MgSO4) and evaporated to dryness to give 5.24 grams of a brown oil. This brown oil was dissolved in toluene and extracted with 2 N hydrochloric acid. The extracts were basified with sodium hydroxide and extracted back into toluene. The resulting solution of the base in toluene was dried (MgSO4) and evaporated to dryness. The resulting oil was crystallised from petrol (100°-120° C.)/toluene affording 2.0 grams of a white solid. This material was dissolved in isopropanol and converted to the hydrochloride salt with ethereal hydrogen chloride and crystallised by addition of ether, yielding 1.153 grams of N-[α-butyl-2-thenyl]-4-pyridinamine hydrochloride of melting point 146.5°-148° C.

Workup

  1. additionwas added dropwise
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-8aedbf9a11e445eb9f21aa8a4ee279d6
Source dataset
uspto-grants-1979_12
Patent number
US04180670

Reaction notes

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