2-Thiophenecarboxylic acid, 3-(isocyanatosulfonyl)-, methyl ester → Methyl 3-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylate

HRID 1979495Notes

Reaction equation

HRID 1979495 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH3:10])[N:3]=1.[CH3:11][O:12][C:13]([C:15]1[S:16][CH:17]=[CH:18][C:19]=1[S:20]([N:23]=[C:24]=[O:25])(=[O:22])=[O:21])=[O:14]>C(#N)C>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([CH3:10])[N:3]=[C:2]([NH:1][C:24]([NH:23][S:20]([C:19]2[CH:18]=[CH:17][S:16][C:15]=2[C:13]([O:12][CH3:11])=[O:14])(=[O:21])=[O:22])=[O:25])[N:7]=1

Participants

4

Reactant 2

HCID 1572962-Thiophenecarboxylic acid, 3-(isocyanatosulfonyl)-, methyl esterHCID 5872364-Methoxy-6-methylpyrimidin-2-amine

Product 1

HCID 13390184Methyl 3-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 1.4 g of 2-amino-4-methoxy-6-methylpyrimidine in 30 ml of anhydrous acetonitrile was added at ambient temperature, with stirring 3.6 g of 2-methoxycarbonyl-3-thiophenesulfonylisocyanate. The mixture was heated to the boiling point and then allowed to cool to ambient temperature. After stirring for sixteen hours the precipitate present in the mixture was filtered off and washed with anhydrous ethyl ether. The product thus obtained which melted at 165°-173° showed absorption peaks by infrared spectroscopy at 1720 and 1700 cm-1, consistent for the carbonyl groups in the desired product.

Workup

  1. temperatureThe mixture was heated to the boiling point
  2. filtrationwas filtered off
  3. washwashed with anhydrous ethyl ether
  4. customThe product thus obtained which melted at 165°-173°
  5. customabsorption peaks by infrared spectroscopy at 1720 and 1700 cm-1

Sources & evidence

ORD record
ord-9017a15b54614e008b0f7c5de8a59418
Source dataset
uspto-grants-1984_11
Patent number
US04481029

Reaction notes

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