Thionyl Chloride → HCID 178433265, compound

HRID 231647Notes

Reaction equation

HRID 231647 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[N:8]=[CH:9][NH:10][C:11]=1[CH3:12]>C(OCC)C>[ClH:3].[CH3:12][C:11]1[N:10]=[CH:9][NH:8][C:7]=1[CH2:6][Cl:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1224334-hydroxymethyl-5-methyl-1H-imidazole

Product 1

HCID 178433265HCID 178433265, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
10 °C

Procedure

Thionyl chloride (50 ml) was stirred under nitrogen in an ice bath while 4-hydroxymethyl-5-methylimidazole (11.2 g, 0.1 m) was added in very small portions over a 15 minute period. The reaction was vigorous and the temperature was maintained between 10° and 20° C. A colorless precipitate formed. When the addition was complete, the temperature was raised slowly (about 1/2 hour) to 55°±5° C. and maintained at that level for about 1/2 hour. The mixture was then cooled to 10° C. and diluted with 100 ml of diethyl ether. The colorless precipitate was collected by filtration, washed well with diethyl ether and dried in air to give 15.23 g (91% yield) of 4-methyl-5-chloromethyl imidazole hydrochloride, m.p. 208°-211° C. (dec.).

Workup

  1. additionwas added in very small portions over a 15 minute period
  2. temperaturethe temperature was maintained between 10° and 20° C
  3. customA colorless precipitate formed
  4. additionWhen the addition
  5. temperaturethe temperature was raised slowly (about 1/2 hour) to 55°±5° C.
  6. temperaturemaintained at that level for about 1/2 hour
  7. filtrationThe colorless precipitate was collected by filtration
  8. washwashed well with diethyl ether
  9. customdried in air

Sources & evidence

ORD record
ord-f31d467381cc461987ef723cf3b6aabb
Source dataset
uspto-grants-1989_07
Patent number
US04847383

Reaction notes

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