Thiourea → HCID 66820895, compound

HRID 523859Notes

Reaction equation

HRID 523859 reaction equation
[Cl:1][CH2:2][C:3]1[N:8]=[C:7]([CH2:9][C:10]#[N:11])[CH:6]=[CH:5][CH:4]=1.[NH2:12][C:13]([NH2:15])=[S:14]>CO>[ClH:1].[C:10]([CH2:9][C:7]1[N:8]=[C:3]([CH2:2][S:14][C:13](=[NH:12])[NH2:15])[CH:4]=[CH:5][CH:6]=1)#[N:11]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 55298443HCID 55298443, compound

Product 1

HCID 66820895HCID 66820895, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 6-chloromethyl-2-pyridylacetonitrile (200 mg, 1.20 mmol) and thiourea (101 mg, 1.32 mmol) were mixed in 1 ml of methanol. The mixture was heated to reflux for 3 to 4 hours. The reaction mixture was evaporated. After that, 1 ml of methanol and 4 ml of acetone were added and the mixture was stirred for one hour. The crystalline material was filtered and the product was dried under high vacuum overnight to yield 216 mg (0.89 mmol, yield 74%) of product as off white crystals, with purity greater than 95%. 1H NMR (300 MHz, d6-DMSO) δ 4.29 (s, 2H), 4.64 (s, 2H), 7.41 (d, 1H, J=7.78), 7.51 (d, 1H, J=7.78), 7.91 (t, 1H, J=7.78), 9.46 (s, 4H). (M+H) 207.00

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 to 4 hours
  3. customThe reaction mixture was evaporated
  4. additionAfter that, 1 ml of methanol and 4 ml of acetone were added
  5. filtrationThe crystalline material was filtered
  6. customthe product was dried under high vacuum overnight

Sources & evidence

ORD record
ord-0bca3d681b2c4b9baece7b8cdbcca83c
Source dataset
uspto-grants-2016_05
Patent number
US09340491B2

Reaction notes

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