Thiourea → HCID 178440260, compound

HRID 1708411Notes

Reaction equation

HRID 1708411 reaction equation
[Na].[NH2:2][C:3]([NH2:5])=[S:4].O=[C:7]([CH2:29][CH2:30][CH3:31])[CH:8]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]#[N:28])=[CH:17][CH:16]=1)[C:9](OCC)=[O:10]>CO>[CH2:29]([C:7]1[N:5]=[C:3]([SH:4])[N:2]=[C:9]([OH:10])[C:8]=1[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]#[N:28])=[CH:19][CH:20]=1)[CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 2723790ThioureaHCID 5360545SodiumHCID 10020734Ethyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate

Product 1

HCID 178440260HCID 178440260, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.7 g of sodium are dissolved in 150 ml of methanol, and 19 g of thiourea are added to this solution. The mixture is stirred for 5 minutes and 58 g of ethyl 3-oxo-2-[(2'-cyano-4-biphenylyl)methyl]hexanoate, prepared in Example 4, are added. The mixture is then heated to reflux for 10 hours and the methanol is evaporated off under vacuum. The residue is taken up with water and washed with ether, the aqueous phase is neutralised by adding dilute hydrochloric acid and the crystals obtained are filtered off and washed with water and with ether to give 26 g of 6-n-propyl-2-mercapto-4-hydroxy-5-[(2'-cyano-4-biphenylyl)methyl]pyrimidine in the form of crystals of melting point 191° C.

Workup

  1. additionare added
  2. temperatureThe mixture is then heated
  3. temperatureto reflux for 10 hours
  4. customthe methanol is evaporated off under vacuum
  5. washwashed with ether
  6. additionby adding dilute hydrochloric acid
  7. customthe crystals obtained
  8. filtrationare filtered off
  9. washwashed with water and with ether

Sources & evidence

ORD record
ord-f28b4c7a81a343fab29f22a5ce1f8cce
Source dataset
uspto-grants-1994_10
Patent number
US05358950

Reaction notes

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