Methane → HCID 19981615, compound

HRID 1460370Notes

Reaction equation

HRID 1460370 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:6]=1[NH2:12])[CH:2]=[CH2:3].[CH3:13][C:14]1[CH:19]=[C:18]([CH3:20])[N:17]2[N:21]=[C:22]([S:24](Cl)(=[O:26])=[O:25])[N:23]=[C:16]2[N:15]=1.[OH-].[Na+].C>N1C=CC=CC=1>[CH3:13][C:14]1[CH:19]=[C:18]([CH3:20])[N:17]2[N:21]=[C:22]([S:24](=[O:25])(=[O:26])[NH:12][C:6]3[C:7]([Cl:11])=[CH:8][CH:9]=[CH:10][C:5]=3[O:4][CH2:1][CH:2]=[CH2:3])[N:23]=[C:16]2[N:15]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 14798Sodium HydroxideHCID 6112325,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonyl chlorideHCID 19981614HCID 19981614, compound

Product 1

HCID 19981615HCID 19981615, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.77g of 2-amino-3-chlorophenyl allyl ether in 12ml of dry pyridine were treated with 1.03g of 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulphonyl chloride and stirred at ambient temperature overnight. The pyridine was removed by evaporation with final traces eliminated by means of a vacuum pump. An oily brown product was obtained which was stirred with 30ml of 1M sodium hydroxide for 20 minutes to give a brown solution. Charcoal (20-30mg) was added and the mixture stirred for 10 minutes and then filtered through Celite ("Celite" is a trade mark). The filtrate was cooled, acidified with 10% hydrochloric acid to pH 1-2 to produce a solid which was then filtered off, washed with water and dried in vacuo to give 1.2g (a yield of 73%) of 5,7-dimethyl-2-(N-[2-allyloxy-6-chlorophenyl]-sulphamoyl)-1,2,4-triazolo[1,5-a]pyrimidine (Compound No. 1).

Workup

  1. customThe pyridine was removed by evaporation with final traces
  2. customAn oily brown product was obtained which
  3. customto give a brown solution
  4. stirringthe mixture stirred for 10 minutes
  5. filtrationfiltered through Celite ("Celite"
  6. temperatureThe filtrate was cooled
  7. customto produce a solid which
  8. filtrationwas then filtered off
  9. washwashed with water
  10. customdried in vacuo

Sources & evidence

ORD record
ord-c2da9a20554a4b648682c109ecd83c03
Source dataset
uspto-grants-1991_12
Patent number
US05071468

Reaction notes

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