Benzene → HCID 15053684, compound

HRID 1073734Notes

Reaction equation

HRID 1073734 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:27]=[CH:26][C:13]([C:14]([N:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][CH2:18][CH2:17]2)=O)=[CH:12][CH:11]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:29].C1C=CC=CC=1.Cl>N1C=CC=CC=1>[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:27]=[CH:26][C:13]([C:14]([N:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][CH2:18][CH2:17]2)=[S:29])=[CH:12][CH:11]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 14817Phosphorus sulfide (P2S5)HCID 15053683HCID 15053683, compound

Product 1

HCID 15053684HCID 15053684, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.77 Gram (2.0 mM) of 1-(4-diethoxyphosphinoylmethylbenzoyl)-1,2,3,4-tetrahydroquinoline and 1.0 g (4.6 mM) of phosphorus pentasulfide were suspended in a mixed solvent consisting of 20 ml of anhydrous benzene and 5 ml of anhydrous pyridine This suspension was heated and refluxed for 7 hours. After the reaction mixture was cooled to room temperature, the mixture was poured into 50 ml of ice-water, and the aqueous phase was acidified with 4N hydrochloric acid and then extracted with chloroform. The chloroform solution was dried over anhydrous sodium sulfate, and concentrated. Thus obtained residue was purified by means of a silica gel column chromatography (eluted with chloroform:ethyl acetate=1:1). The crude crystals were recrystallized from benzene-n-hexane to yield 0.23 g of 1-[(4-diethoxyphosphinoylmethylphenyl)thiocarbonyl]-1,2,3,4-tetrahydroquinoline as yellowish crystals. Melting point 96°-97° C.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed for 7 hours
  3. extractionextracted with chloroform
  4. dry with materialThe chloroform solution was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThus obtained residue was purified by means of a silica gel column chromatography (eluted with chloroform:ethyl acetate=1:1)
  7. customThe crude crystals were recrystallized from benzene-n-hexane

Sources & evidence

ORD record
ord-09cde3db19a64b23b72839c867350837
Source dataset
uspto-grants-1990_11
Patent number
US04971957

Reaction notes

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