Hydrochloric Acid → HCID 22397431, compound

HRID 349760Notes

Reaction equation

HRID 349760 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:8]([C:10]#[N:11])[CH:9]=1)=[O:4].[Li+].[OH-].Cl.C(C1C=C(C(O)=O)SC=1S(C)(=O)=[O:27])#N>C1COCC1.O>[C:10]([C:8]1[CH:9]=[C:5]([C:3]([OH:2])=[O:4])[S:6][C:7]=1[S:12]([CH3:15])(=[O:14])=[O:13])(=[O:27])[NH2:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 4128981HCID 4128981, compoundHCID 22397444HCID 22397444, compound

Product 1

HCID 22397431HCID 22397431, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To 4-cyano-5-methanesulfonyl-thiophene-2-carboxylic acid methyl ester (0.5 g) in THF/H2O (3:1; 16 ml) was added LiOH (0.102 g). Hydrochloric acid (2M) was added and the resulting mixture was extracted with ethyl acetate. The extracts were combined and the solvent evaporated to leave a mixture of 4-cyano-5-methanesulfonyl-thiophene-2-carboxylic acid and the title compound. This mixture was used without further purification. 1H NMR (299.944 MHz, DMSO-D6) δ 3.62 (3H, s), 7.99 (1H, s).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. customthe solvent evaporated
  3. customto leave

Sources & evidence

ORD record
ord-297b1915dfdd42ceadd787c7f88ae472
Source dataset
uspto-grants-2007_02
Patent number
US07179922B2

Reaction notes

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