5-Chlorovaleronitrile → S-(4-cyanobutyl)isothiourea hydrochloride

HRID 523855

Reaction equation

HRID 523855 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[N:7].[NH2:8][C:9]([NH2:11])=[S:10]>O>[ClH:1].[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][S:10][C:9](=[NH:8])[NH2:11])#[N:7]

Participants

4

Reactant 2

HCID 804745-ChlorovaleronitrileHCID 2723790Thiourea

Product 1

HCID 86647987S-(4-cyanobutyl)isothiourea hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The 5-chloropentanenitrile (5.68 g, 48.3 mmol) and thiourea (4.04 g, 53.1 mmol) are mixed in 40 ml of water. The mixture is heated to reflux for 3 to 4 hours. The reaction mixture is evaporated and 20 ml of ethanol are added and then evaporated as well. This is repeated three times. After that, 10 ml of methanol and 30 ml of acetone are added and the mixture is stirred for one hour. The crystalline material is filtered and the product is dried under high vacuum overnight to yield S-(4-cyanobutyl)isothiourea hydrochloride.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 3 to 4 hours
  3. customThe reaction mixture is evaporated
  4. addition20 ml of ethanol are added
  5. customevaporated as well
  6. additionAfter that, 10 ml of methanol and 30 ml of acetone are added
  7. filtrationThe crystalline material is filtered
  8. customthe product is dried under high vacuum overnight

Sources & evidence

ORD record
ord-ca8ee209e9404743b3685cba14b1dcee
Source dataset
uspto-grants-2016_05
Patent number
US09340491B2

Linked notes

Loading…