Lithium iodide → HCID 15734853, compound

HRID 1030222Notes

Reaction equation

HRID 1030222 reaction equation
[C:1]([N:3]=[C:4]1[N:8]([C:9]2[C:14]3[CH:15]=[C:16]([C:19]([O:21]CC)=[O:20])[CH:17]=[CH:18][C:13]=3[O:12][C:11]([CH3:25])([CH3:24])[CH:10]=2)[CH2:7][CH2:6][S:5]1)#[N:2].[I-].[Li+]>N1C(C)=CC=CC=1C.C(OCC)(=O)C.Cl>[C:1]([N:3]=[C:4]1[N:8]([C:9]2[C:14]3[CH:15]=[C:16]([C:19]([OH:21])=[O:20])[CH:17]=[CH:18][C:13]=3[O:12][C:11]([CH3:25])([CH3:24])[CH:10]=2)[CH2:7][CH2:6][S:5]1)#[N:2]

Participants

6

Reactant 2

HCID 66321Lithium iodideHCID 15734813HCID 15734813, compound

Product 1

HCID 15734853HCID 15734853, compoundYield 59.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 79372,6-LutidineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl 4-(2-cyanoiminothiazolidin-3-yl)-2,2-dimethyl-2H-1-benzopyran-6-carboxylate (1.15 g) and lithium iodide (3.44 g) in 2,6-lutidine (11.5 ml) was refluxed overnight. The resulting mixture was dissolved in a mixture of ethyl acetate and 10% hydrochloric acid, and the organic layer was separated and washed with brine. The extract was dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (elution with 30:1 to 4:1 chloroform-methanol) followed by recrystallization from ethanol to give 4-(2-cyanoiminothiazolidin-3-yl)-2,2-dimethyl-2H-1-benzopyran-6-carboxylic acid (0.63 g).

Workup

  1. temperaturewas refluxed overnight
  2. customthe organic layer was separated
  3. washwashed with brine
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (elution with 30:1 to 4:1 chloroform-methanol)
  7. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-922fc923eaa7455b8e9bdd34967bc70d
Source dataset
uspto-grants-1992_04
Patent number
US05104890

Reaction notes

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