Thionyl Chloride → 1-(Chloromethyl)-1H-benzotriazole

HRID 487844Notes

Reaction equation

HRID 487844 reaction equation
O[CH2:2][N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[N:4]1.S(Cl)([Cl:14])=O>>[Cl:14][CH2:2][N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[N:4]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 2241691H-Benzotriazole-1-methanol

Product 1

HCID 33282221-(Chloromethyl)-1H-benzotriazole

Procedure

To 1-hydroxymethylbenzotriazole (59.6 g), prepared above, kept at ice-bath temp., 175 ml of thionyl chloride was added dropwise as long as a vigorous reaction continued. The reminder was added more rapidly. The mixture was then stirred and refluxed for 90 minutes. Excess thionyl chloride was removed by distillation, the last traces were removed by heating for a short time with 200 ml of methanol. After cooling and collecting on a funnel, the product weighted 45 g. (67%); melting point: 136° C; (lit. 136°-138° C.).

Workup

  1. customkept at ice-bath
  2. customlong as a vigorous reaction
  3. additionThe reminder was added more rapidly
  4. temperaturerefluxed for 90 minutes
  5. customExcess thionyl chloride was removed by distillation
  6. customthe last traces were removed
  7. temperatureby heating for a short time with 200 ml of methanol
  8. temperatureAfter cooling
  9. customcollecting on a funnel
  10. custom(lit. 136°-138° C.)

Sources & evidence

ORD record
ord-7177162652f94555b6c1f096e402f1e6
Source dataset
uspto-grants-1994_03
Patent number
US05298390

Reaction notes

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