2-Hydroxy benzimidazole → Ethyl 4-methylthiophene-2-carboxylate

HRID 2394356Notes

Reaction equation

HRID 2394356 reaction equation
ClC1C=C2C(C([C:12](=[O:19])[C:13]3[S:17][CH:16]=[C:15]([CH3:18])[CH:14]=3)C(=O)N2)=NC=1.ClC1C=C2C([CH2:25][C:26](=[O:30])N2)=NC=1.CC1C=C(C(Cl)=O)SC=1.[O-]CC.[Na+].N1C2C(=CC=CC=2)NC1=O>C(O)C>[CH2:26]([O:30][C:12]([C:13]1[S:17][CH:16]=[C:15]([CH3:18])[CH:14]=1)=[O:19])[CH3:25]

Participants

7

Reactant 5

HCID 119852-Hydroxy benzimidazoleHCID 2723922Sodium ethoxideHCID 27955254-Methylthiophene-2-carbonyl chlorideHCID 104873236-Chloro-1,3-dihydropyrrolo[3,2-B]pyridin-2-oneHCID 189730706-Chloro-3-(4-methyl-2-thenoyl)-4-azaoxindole

Product 1

HCID 18973097Ethyl 4-methylthiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Chloro-3-(4-methyl-2-thenoyl)-4-azaoxindole was first prepared according to a variation of the procedure of Example 2B, using 6-chloro-4-azaoxindole (1.3 g, 7.71 mmol) sodium (1.75 g, 49.7 mmol), 4-methylthiophene-2-carbonyl chloride (1.93 g, 12.0 mmol) and ethanol (40 mL). Ethyl-4-methylthiophene-2-carboxylate was prepared in situ by addition of the acid chloride to the sodium ethoxide solution. The azaoxindole was added and the reaction carried out as in Example 1B. Yield: 1.64 g (46%) m.p.>250°.

Sources & evidence

ORD record
ord-e0fbf4b831c948d5917bf5523cce7d72
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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