Hydrochloric Acid → HCID 13389105, compound

HRID 638348Notes

Reaction equation

HRID 638348 reaction equation
[C:1]1([CH:7]2[CH2:11][N:10]3[CH2:12][CH2:13][CH2:14][C:9]3=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.[Cl:20]C1C=CC=C(Cl)C=1S[S:29][C:30]1[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=1[Cl:37].Cl>>[ClH:20].[C:1]1([CH:7]2[CH2:11][N:10]3[CH2:12][CH2:13][CH:14]([S:29][C:30]4[C:31]([Cl:37])=[CH:32][CH:33]=[CH:34][C:35]=4[Cl:36])[C:9]3=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 588476Bis(2,6-dichlorophenyl) disulfideHCID 12258399HCID 12258399, compoundHCID 178418339Butyllithium

Product 1

HCID 13389105HCID 13389105, compoundYield 40.7%

Procedure

2,5,6,7-Tetrahydro-2-phenyl-3H-pyrrolo[1,2-a]imidazole was reacted with 2 equivalents of n-BuLi and 1 equivalent of 2,6-dichlorophenyldisulfide according to the general procedure A above except that when the reaction mixture was poured into the aq HCl solution, the HCl salt of the desired product precipitated. It was collected, washed well with cold H2O, then Et2O and dried in vacuo; yield 40.7%; m.p. 96°-99°. Neutralization of the acidic filtrate with NaHCO3, followed by extraction with Et2O, yielded an additional amount of the desired product as the free base (39.2%).

Workup

  1. customthe HCl salt of the desired product precipitated
  2. customIt was collected
  3. washwashed well with cold H2O
  4. dry with materialEt2O and dried in vacuo
  5. extractionNeutralization of the acidic filtrate with NaHCO3, followed by extraction with Et2O

Sources & evidence

ORD record
ord-12b5ebb086d548b4b93ee812547f2d85
Source dataset
uspto-grants-1985_12
Patent number
US04560758

Reaction notes

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