Allyl Alcohol → 5-Allyloxy-8,9-dimethoxy-1,2,4-triazolo[1,5-c]quinazoline

HRID 972714Notes

Reaction equation

HRID 972714 reaction equation
[CH2:1]([OH:4])[CH:2]=[CH2:3].Cl[C:6]1[N:15]2[CH:16]=[N:17][N:18]=[C:14]2[C:13]2[CH:12]=[C:11]([O:19][CH3:20])[C:10]([O:21][CH3:22])=[CH:9][C:8]=2[N:7]=1>>[CH2:1]([O:4][C:6]1[N:18]2[N:17]=[CH:16][N:15]=[C:14]2[C:13]2[CH:12]=[C:11]([O:19][CH3:20])[C:10]([O:21][CH3:22])=[CH:9][C:8]=2[N:7]=1)[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 7858Allyl Alcohol2×HCID 214051435-Chloro-8,9-dimethoxy-1,2,4-triazolo[4,3-c]quinazoline

Product 1

HCID 214051325-Allyloxy-8,9-dimethoxy-1,2,4-triazolo[1,5-c]quinazoline

Procedure

To 65 ml. of allyl alcohol cooled to room temperature is added 2.8 g. of sodiuom followed by addition of an additional 120 ml. of allyl alcohol. To the resulting mixture at room temperature is added 15.0 g. of 5-chloro-8,9-dimethoxy-1,2,4-triazolo[4,3-c]quinazoline. The resulting precipitate is filtered off, washed with diethyl ether, dissolved in methylene chloride, washed with water, dried and evaporated in vacuo to dryness. The residue is twice crystallized from ethanol after treatment with charcoal to obtain 5-allyloxy-8,9-dimethoxy-1,2,4-triazolo[1,5-c]quinazoline, m.p. 189°-191° C.

Workup

  1. additionis added 2.8 g
  2. additionof sodiuom followed by addition of an additional 120 ml
  3. additionTo the resulting mixture at room temperature is added 15.0 g
  4. filtrationThe resulting precipitate is filtered off
  5. washwashed with diethyl ether
  6. dissolutiondissolved in methylene chloride
  7. washwashed with water
  8. customdried
  9. customevaporated in vacuo to dryness
  10. customThe residue is twice crystallized from ethanol after treatment with charcoal

Sources & evidence

ORD record
ord-aae9ea9e6ce9462eb63f58759a005cbf
Source dataset
uspto-grants-1977_10
Patent number
US04053600

Reaction notes

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