Thionyl Chloride → 2-Chloromethyl-3-triphenylmethylthiopyridine hydrochloride

HRID 2085992

Reaction equation

HRID 2085992 reaction equation
O[CH2:2][C:3]1[C:8]([S:9][C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=[CH:5][N:4]=1.S(Cl)([Cl:31])=O>CN(C)C=O>[ClH:31].[Cl:31][CH2:2][C:3]1[C:8]([S:9][C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 99080472-Hydroxymethyl-3-triphenylmethylthiopyridine

Product 1

HCID 98459692-Chloromethyl-3-triphenylmethylthiopyridine hydrochlorideYield 111.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
2 °C

Procedure

A thick suspension of 2-hydroxymethyl-3-triphenylmethylthiopyridine (90.3 g, 235 mmol) in N,N-dimethylformamide (270 mL) in a flask equipped with efficient mechanical stirring was chilled to 2° C. Thionyl chloride (25.8 mL, 354 mmol) was added in 5 mL portions over the period of 1 h while maintaining a temperature below 10° C. After completing the addition the reaction mixture was allowed to reach room temperature and was stirred for 30 min. The precipitate was filtered, washed with ethyl acetate (500 mL) and dried to give 86.7 g (84%) 2-chloromethyl-3-triphenylmethylthiopyridine hydrochloride as colorless crystals.

Workup

  1. customequipped with efficient
  2. temperaturewhile maintaining a temperature below 10° C
  3. additionthe addition the reaction mixture
  4. customto reach room temperature
  5. stirringwas stirred for 30 min
  6. filtrationThe precipitate was filtered
  7. washwashed with ethyl acetate (500 mL)
  8. customdried

Sources & evidence

ORD record
ord-ed4386c655034ee58cd48866a7e3d073
Source dataset
uspto-grants-2004_04
Patent number
US06723716B1

Linked notes

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