Hydrochloric Acid → 4-Amino-6-(2,4-dichlorophenyl)pyrimidine-2(1H)-thione

HRID 2171472

Reaction equation

HRID 2171472 reaction equation
[Na].[NH2:2][C:3]([NH2:5])=[S:4].C([O-])C.[Na+].N[C:11]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22])=[CH:12][C:13]#[N:14].Cl>C(O)C.O>[NH2:14][C:13]1[CH:12]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[NH:5][C:3](=[S:4])[N:2]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 2723790ThioureaHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 669113223-Amino-3-(2,4-dichlorophenyl)acrylonitrile

Product 1

HCID 583059934-Amino-6-(2,4-dichlorophenyl)pyrimidine-2(1H)-thione

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

16.51 g (718.08 mmol) of sodium are dissolved in 353 ml of ethanol, and 40.996 g (538.56 mmol) of thiourea are added to the sodium ethanolate solution prepared in this way, followed by 76.5 g (359.04 mmol) of 3-amino-3-(2,4-dichlorophenyl)acrylonitrile. The mixture is heated under reflux for 18 h and, after cooling, 500 ml of water are added. The mixture is neutralized with 1M hydrochloric acid, and the precipitate which has separated out is filtered off with suction. The latter is washed with water, suspended in THF and again filtered off with suction. It is washed with 300 ml of petroleum ether and then dried under high vacuum. 67.5 g (55% of theory) of the product are obtained as a solid.

Workup

  1. customprepared in this way
  2. temperatureThe mixture is heated
  3. temperatureunder reflux for 18 h
  4. temperatureafter cooling
  5. customthe precipitate which has separated out
  6. filtrationis filtered off with suction
  7. washThe latter is washed with water
  8. filtrationagain filtered off with suction
  9. washIt is washed with 300 ml of petroleum ether
  10. customdried under high vacuum
  11. custom67.5 g (55% of theory) of the product are obtained as a solid

Sources & evidence

ORD record
ord-7388652bd41144639ea28a102170f284
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Linked notes

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