Thiourea → s-(2-Cyanomethylphenyl)methylisothiourea hydrochloride

HRID 523858Notes

Reaction equation

HRID 523858 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]#[N:11].[NH2:12][C:13]([NH2:15])=[S:14]>CO>[ClH:1].[C:10]([CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][S:14][C:13](=[NH:12])[NH2:15])#[N:11]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 112981592-(Cyanomethyl)benzyl chloride

Product 1

HCID 66818824s-(2-Cyanomethylphenyl)methylisothiourea hydrochlorideYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 2-chlormethylphenylacetonitrile (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 231 mg (0.95 mmol, yield 79%) of product as off white crystals, with purity greater than 95%. 1H NMR (300 MHz, d6-DMSO) δ 4.14 (s, 2H), 4.56 (s, 2H), 7.37 (m, 2H), 7.45 (m, 2H), 9.23 (s, 4H). (M+H) 205.97

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-49de244389764d50a4050827217a1c0d
Source dataset
uspto-grants-2016_05
Patent number
US09340491B2

Reaction notes

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