Triethylamine → HCID 18536768, compound

HRID 2298625Notes

Reaction equation

HRID 2298625 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:12]([O:14][CH3:15])=[O:13])[S:6][C:7]=1[S:8]([CH3:11])(=O)=O)#[N:2].[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21](CS)=[CH:20][CH:19]=1.C(N(CC)CC)C>CO>[C:1]([C:3]1[CH:4]=[C:5]([C:12]([O:14][CH3:15])=[O:13])[S:6][C:7]=1[S:8][CH2:11][C:21]1[CH:24]=[CH:25][C:18]([O:17][CH3:16])=[CH:19][CH:20]=1)#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 804074-Methoxy-alpha-toluenethiolHCID 4128981HCID 4128981, compound

Product 1

HCID 18536768HCID 18536768, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2.5 g (10 mmol) of methyl 4-cyano-5-(methylsulfonyl)thiophene-2-carboxylate (Example 139, step (a)) in dry methanol (15 mL) was added p-methoxybenzylmercaptan (3.8 mL, 28 mmol) and triethylamine (1.4 mL, 10 mmol). This solution was refluxed for 15 min and cooled. The resulting solid was collected on a buchner funnel and washed with methanol (2×25 mL) to methyl 4-cyano-5-[(4-methoxyphenyl)methylthio]thiophene-2-carboxylate (2.84 g, 89%) as a solid.

Workup

  1. temperatureThis solution was refluxed for 15 min
  2. temperaturecooled
  3. customThe resulting solid was collected on a buchner funnel
  4. washwashed with methanol (2×25 mL) to methyl 4-cyano-5-[(4-methoxyphenyl)methylthio]thiophene-2-carboxylate (2.84 g, 89%) as a solid

Sources & evidence

ORD record
ord-dfbbbb965a8b4383a93a3b454a88d4f6
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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