Formamide → HCID 136378636, compound

HRID 2408974Notes

Reaction equation

HRID 2408974 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([S:7][CH3:8])[S:4][C:3]=1[C:9]([O:11]CC)=O.[CH:14]([NH2:16])=O>>[CH3:8][S:7][C:5]1[S:4][C:3]2[C:9](=[O:11])[NH:16][CH:14]=[N:1][C:2]=2[CH:6]=1

Participants

3

Reactant 2

HCID 713FormamideHCID 69671703HCID 69671703, compound

Product 1

HCID 136378636HCID 136378636, compoundYield 61%

Conditions

Temperature
155 °C

Procedure

A mixture of ethyl 3-amino-5-(methylthio)-thiophene-2-carboxylate (2 g) and formamide (20 mL) was stirred at 150-160° C. for 6 h. The reaction mixture was allowed to rt and poured into ice cold water. The solution was stirred for 15 min. and the precipitated solid was filtered, washed with ice cold water and dried to give the product as a light brown color solid (1.2 g, 61%), mp 216-218° C. 1H NMR (400 MHz, DMSO-d6): δ 12.45 (1H, s), 8.11 (1H, s), 7.26 (1H, s), 2.68 (3H, s); LC-MS (negative ion mode): m/z 197 (M−H)−.

Workup

  1. customwas allowed to rt
  2. additionpoured into ice cold water
  3. stirringThe solution was stirred for 15 min.
  4. filtrationthe precipitated solid was filtered
  5. washwashed with ice cold water
  6. customdried

Sources & evidence

ORD record
ord-b475ea21f0e44657b96bd478177e2baa
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

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