Water → HCID 13559525, compound

HRID 638589Notes

Reaction equation

HRID 638589 reaction equation
B(Cl)(Cl)Cl.C(Cl)Cl.[Cl:8][C:9]1[N:14]2[N:15]=[CH:16][N:17]=[C:13]2[C:12]([CH2:18][CH2:19][O:20]CC)=[C:11]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:10]=1.O>C(Cl)(Cl)Cl>[Cl:8][C:9]1[N:14]2[N:15]=[CH:16][N:17]=[C:13]2[C:12]([CH2:18][CH2:19][OH:20])=[C:11]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 13559523HCID 13559523, compound

Product 1

HCID 13559525HCID 13559525, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Under non-aqueous conditions 200 ml of a mixture of boron trichloride (0.2 mol) and methylene chloride (1 mol) is added over a period of 20 minutes with vigorous stirring to a solution containing 30 g of 5-chloro-8-(2-ethoxyethyl)-7-phenyl[1,2,4]triazolo[1,5-c]pyrimidine (0.1 moles) dissolved in 300 ml of chloroform. The resulting reaction mixture is stirred at room temperature for 3 hours. To the reaction mixture is added 400 ml of water and the resulting mixture is stirred for 1.5 hours and then allowed to stand at room temperature. The aqueous and organic layers are separated and the organic layer is dried over sodium sulfate, filtered and evaporated yielding a residue. The residue is chromatographed on silica gel and recrystallized from diethyl ether to yield 5-chloro-7-phenyl[1,2,4]triazolo[1,5-c]pyrimidine-8-ethanol having the structural formula ##STR21## and the azido tautomer thereof as a white solid having a melting point of 104°-105° C. and the following elemental analysis:

Workup

  1. customThe resulting reaction mixture
  2. stirringis stirred at room temperature for 3 hours
  3. stirringthe resulting mixture is stirred for 1.5 hours
  4. customto stand at room temperature
  5. customThe aqueous and organic layers are separated
  6. dry with materialthe organic layer is dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customyielding a residue
  10. customThe residue is chromatographed on silica gel
  11. customrecrystallized from diethyl ether

Sources & evidence

ORD record
ord-677ab3a93f4040db9ca2a35bb0a6669e
Source dataset
uspto-grants-1985_12
Patent number
US04562192

Reaction notes

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