Thiourea → HCID 66820877, compound

HRID 2196463Notes

Reaction equation

HRID 2196463 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.[NH2:12][C:13]([NH2:15])=[S:14]>CO>[ClH:1].[C:10]([CH2:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][S:14][C:13](=[NH:12])[NH2:15])=[CH:4][CH:5]=1)#[N:11]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 1174499166736-53-6

Product 1

HCID 66820877HCID 66820877, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 4-chloromethylphenylacetonitrile (200 mg, 1.21 mmol) and thiourea (101 mg, 1.33 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 219 mg (0.91 mmol, yield 75%) of product as off white crystals, with purity greater than 95%. 1H NMR (300 MHz, d6-DMSO) 4.03 (s, 2H), 4.50 (s, 2H), 7.35 (d, 2H, J=8.23 Hz), 7.45 (d, 2H, J=8.23 Hz), 9.22 (s, 4H). (M+H) 206.00

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-77e6d2db69d0471f8e732c0722c1a9a3
Source dataset
uspto-grants-2012_12
Patent number
US08338454B2

Reaction notes

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