O-Toluidine → HCID 178424356, compound

HRID 1198107Notes

Reaction equation

HRID 1198107 reaction equation
C(S[C:4]1[N:5]=[C:6]([OH:13])[C:7]2[S:12][CH:11]=[CH:10][C:8]=2[N:9]=1)C.[NH2:14][C:15]1[C:16]([CH3:21])=[CH:17][CH:18]=[CH:19][CH:20]=1>C(OCC)C>[CH3:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[NH:14][C:4]1[N:5]=[C:6]([OH:13])[C:7]2[S:12][CH:11]=[CH:10][C:8]=2[N:9]=1

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 178477354HCID 178477354, compound

Product 1

HCID 178424356HCID 178424356, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-Ethylmercapto-4-hydroxythieno[3,2-d]pyrimidine 10 g, 0.047I mol) and o-toluidine (30 g, 0.0279 mol) were heated in an oil bath at 210° for 20 hours. The reaction mixture was poured into diethyl ether and the solid obtained was collected by filtration and dried. The mother liquor was extracted with 2N sodium hydroxide (3×100 ml). The aqueous extracts were combined, acidified with glacial acetic acid and extracted with chloroform (3×100 ml). The chloroform extracts were combined, dried over magnesium sulphate, filtered and evaporated under reduced pressure to give a solid. Recrystallization from methanol gave a pure sample, (5.32 g), m.p. 243°-245°.

Workup

  1. customthe solid obtained
  2. filtrationwas collected by filtration
  3. customdried
  4. extractionThe mother liquor was extracted with 2N sodium hydroxide (3×100 ml)
  5. extractionextracted with chloroform (3×100 ml)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customto give a solid
  10. customRecrystallization from methanol
  11. customgave a pure sample, (5.32 g), m.p. 243°-245°

Sources & evidence

ORD record
ord-99e377b1c1524d8591db0797514c2f90
Source dataset
uspto-grants-1994_01
Patent number
US05280026

Reaction notes

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