Hydrochloric Acid → HCID 44416749, compound

HRID 1990110Notes

Reaction equation

HRID 1990110 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]([S:23][CH3:24])=[C:9]([C:21]#[N:22])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=1)=[O:5])C.[OH-].[Li+].Cl>C1COCC1.CO.O>[C:17]([C:14]1[CH:13]=[CH:12][C:11]([C:10]2[C:9]([C:21]#[N:22])=[C:8]([S:23][CH3:24])[O:7][C:6]=2[C:4]([OH:5])=[O:3])=[CH:16][CH:15]=1)([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58873068HCID 58873068, compound

Product 1

HCID 44416749HCID 44416749, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Dissolve 3-(4-tert-butyl-phenyl)-4-cyano-5-methylsulfanyl-furan-2-carboxylic acid ethyl ester (110 mg, 0.32 mmol) in a solution of THF: MeOH: H2O (3:2:1, 5 ml). Add lithium hydroxide (80 mg, 3.3 mmol) to the mixture and stir the reaction at 60° C. for 30 minutes. Add 6N HCl until pH approx. 1 to obtain the desired white solid of the titled compound (30 mg, 30%): Mass spectrum (M−1)=314. EA, Calculated: C; 61.91, H; 5.68, N; 4.25. Found: C; 61.75, H; 5.42, N; 3.91.

Workup

  1. customthe reaction at 60° C. for 30 minutes

Sources & evidence

ORD record
ord-9a19d2a6a62a497a966461e1b85ab492
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

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