Ethyl orthoformate → HCID 178482140, compound

HRID 622711

Reaction equation

HRID 622711 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([C:10]2[CH:11]=[C:12]([NH2:16])[CH:13]=[CH:14][CH:15]=2)[N:9]=1)[C:2]([NH2:4])=[NH:3].[CH2:17](OC(OCC)OCC)C>FC(F)(F)C(O)=O>[NH:1]([C:5]1[S:6][CH:7]=[C:8]([C:10]2[CH:11]=[C:12]([NH:16][CH3:17])[CH:13]=[CH:14][CH:15]=2)[N:9]=1)[C:2]([NH2:4])=[NH:3]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 1785126111-(4-(3-Aminophenyl)thiazol-2-yl)guanidine

Product 1

HCID 178482140HCID 178482140, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidCatalyst

Conditions

Temperature
0 °C

Procedure

A mixture of 9.3 g (0.04 mole) of 3-(2-guanidino-4-thiazolyl)benzeneamine, 20 ml of triethylorthoformate, and 2 drops of trifluoroacetic acid is stirred at reflux for 5 hours after which it is concentrated in vacuo. The residue is dissolved in 20 ml of ethanol, the solution cooled to 0° C. and then treated with excess sodium borohydride. The mixture is allowed to warm to room temperature, then stirred at reflux for 4 hours. Upon concentration in vacuo the residue is partitioned between water and dichloromethane.

Workup

  1. temperatureat reflux for 5 hours after which it
  2. concentrationis concentrated in vacuo
  3. dissolutionThe residue is dissolved in 20 ml of ethanol
  4. additiontreated with excess sodium borohydride
  5. temperatureto warm to room temperature
  6. stirringstirred
  7. temperatureat reflux for 4 hours
  8. concentrationUpon concentration in vacuo the residue
  9. customis partitioned between water and dichloromethane

Sources & evidence

ORD record
ord-bf26f55371854a828c4f5bb935c679d5
Source dataset
uspto-grants-1988_09
Patent number
US04772622

Linked notes

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