2-Thiophenecarboxaldehyde → 2-Cyano-3-thiophen-2-yl-thioacrylamide

HRID 2375360Notes

Reaction equation

HRID 2375360 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[C:8]([CH2:10][C:11]([NH2:13])=[S:12])#[N:9].CN1CCOCC1>C(O)C>[C:8]([C:10](=[CH:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[C:11]([NH2:13])=[S:12])#[N:9]

Participants

5

Reactant 3

HCID 73642-ThiophenecarboxaldehydeHCID 79724-MethylmorpholineHCID 14162772-Cyanoethanethioamide

Product 1

HCID 27298552-Cyano-3-thiophen-2-yl-thioacrylamideYield 72.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2-thiophencarbaldehyde (22.4 g, 0.2 mol) and 2-cyanothioacetamide (22 g, 0.22 mol) in 250 ml of ethanol was added N-methylmorpholine (30.3 g, 0.3 mol) at room temperature. The resulting mixture was stirred at room temperature overnight. The solid was filtered and washed with ethanol to give 28.2 g (72%) of product as a yellow solid after drying in vacuo. 1H-NMR (300 MHz, DMSO-d6): δ 10.0 (brs, 1H), 9.45 (brs, 1H), 8.37 (s, 1H), 8.12 (d, J=4.8 Hz, 1H), 7.88 (d, J=3.3 Hz, 1H), 7.32 (dd, J=3.3, 4.8 Hz, 1H). ES MS m/z 195 (M+H)+, 193(M−H)−.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with ethanol

Sources & evidence

ORD record
ord-cf3304bc97c541cf86b4e07ffa3726a7
Source dataset
uspto-grants-2008_12
Patent number
US07465742B2

Reaction notes

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