Water → 2-(Chloromethyl)-4-phenyl-1,3-thiazole

HRID 1112730Notes

Reaction equation

HRID 1112730 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[S:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:11]=1.N1C=CC=CC=1.O>C1C=CC=CC=1>[Cl:3][CH2:6][C:7]1[S:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 698895(4-Phenyl-1,3-thiazol-2-yl)methanol

Product 1

HCID 225573612-(Chloromethyl)-4-phenyl-1,3-thiazole

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Thionyl chloride (6.25 g, 0.052 mole) was added dropwise to a stirred solution of 2-hydroxymethyl-4-phenylthiazole (9.55 g; 0.05 mole) and dry pyridine (4.0 g; 0.051 mole) in dry benzene (60 ml) held at room temperature. The mixture was stirred and heated to boiling for 1 hour. The cooled reaction mixture was then shaken with 2 × 70 ml H2O and dried over anhydrous MgSO4. The solvent was removed under vacuum and the remaining red oil extracted with 40°-60° C. petroleum ether (100 ml), discarding a small tarry residue. The extract was treated with decolourising charcoal, filtered and evaporated, leaving a yellow-red oil that crystallised on refrigeration.

Workup

  1. customheld at room temperature
  2. temperatureheated
  3. customThe cooled reaction mixture
  4. dry with materialdried over anhydrous MgSO4
  5. customThe solvent was removed under vacuum
  6. extractionthe remaining red oil extracted with 40°-60° C. petroleum ether (100 ml)
  7. additionThe extract was treated with decolourising charcoal
  8. filtrationfiltered
  9. customevaporated
  10. customleaving a yellow-red oil that
  11. customcrystallised on refrigeration

Sources & evidence

ORD record
ord-1368ec37672d4543a163542ef31769aa
Source dataset
uspto-grants-1978_10
Patent number
US04123529

Reaction notes

Loading…