Hydrochloric Acid → HCID 178507270, compound

HRID 1852962Notes

Reaction equation

HRID 1852962 reaction equation
[Na].[NH2:2][C:3]([NH2:5])=[S:4].N[C:7]([C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)=[CH:8][C:9]#[N:10].Cl>S([O-])([O-])(=O)=O.[Cu+2].O.C(O)C>[NH2:10][C:9]1[NH:5][C:3](=[S:4])[N:2]=[C:7]([C:11]2[CH:12]=[CH:13][C:14]([Br:17])=[CH:15][CH:16]=2)[CH:8]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 738032HCID 738032, compoundHCID 2723790ThioureaHCID 5360545Sodium

Product 1

HCID 178507270HCID 178507270, compoundYield 110.8%

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a flask charged with 600 mL of absolute ethanol was dissolved sodium (14.86 g, 646.5 mmol) with a catalytic amount of copper(II)sulfate (10 mg). The reaction volume was reduced by half under reduced pressure and thiourea (49.22 g, 646.5 mmol) and 3-amino-3-(4-bromophenyl)acrylonitrile (38.46 g, 172.4 mmol) were added at ambient temperature and the reaction mixture was fitted with a condenser and heated to reflux over the weekend. Water (400 mL) was added and the mixture was made acidic with concentrated aqueous hydrochloric acid to a pH=7. The reaction mixture was allowed to stir for 5 minutes and the resulting solids were collected by means of vacuum filtration and afforded 6-amino-4-(4-bromophenyl)pyrimidine-2(1H)-thione (53.90 g, 191.0 mmol, 110.8% yield). MS (apci) m/z=282.0 (M+H).

Workup

  1. additionwere added at ambient temperature
  2. customthe reaction mixture was fitted with a condenser
  3. temperatureheated
  4. temperatureto reflux over the weekend
  5. filtrationthe resulting solids were collected by means of vacuum filtration

Sources & evidence

ORD record
ord-1c5d592cca204d4f971099818337a972
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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