Chlorine → HCID 178517816, compound

HRID 1580437Notes

Reaction equation

HRID 1580437 reaction equation
[C:1]1([N:7]2[CH:11]=[N:10][C:9]([OH:12])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:13]Cl>C(N(CC)CC)C>[C:1]1([N:7]2[C:11]([Cl:13])=[N:10][C:9]([OH:12])=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 24526ChlorineHCID 178517978HCID 178517978, compound

Product 1

HCID 178517816HCID 178517816, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

32.2 g of 1-phenyl-3-hydroxy-1,2,4-triazole and 40.5 g of triethylamine are dissolved in 300 ml of absolute alcohol. While cooling, 21.3 g of chlorine are passed in (20° to 30°C). Triethylamino hydrochloride is filtered off and the filtrate is concentrated in a rotary evaporator. The residue is treated with 300 ml of water and extracted 4 times with 200 ml of ether each time. The combined ethereal extracts are dried over sodium sulphate. The drying agent is filtered off and the filtrate concentrated. The solid residue is recrystallised from 70 ml of acetonitrile. Yield: 11.4 g (29.2 % of theory); m.p. 147°-149°C.

Workup

  1. temperatureWhile cooling
  2. customare passed in (20° to 30°C)
  3. filtrationTriethylamino hydrochloride is filtered off
  4. concentrationthe filtrate is concentrated in a rotary evaporator
  5. additionThe residue is treated with 300 ml of water
  6. extractionextracted 4 times with 200 ml of ether each time
  7. dry with materialThe combined ethereal extracts are dried over sodium sulphate
  8. filtrationThe drying agent is filtered off
  9. concentrationthe filtrate concentrated
  10. customThe solid residue is recrystallised from 70 ml of acetonitrile

Sources & evidence

ORD record
ord-1f7aae7157c14c18a35cf056236dd743
Source dataset
uspto-grants-1976_01
Patent number
US03932629

Reaction notes

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