Thionyl Chloride → 1-{4-[4-(Chloromethyl)-5-methyl-1,3-oxazol-2-yl]benzyl}-1H-benzimidazole

HRID 1716832Notes

Reaction equation

HRID 1716832 reaction equation
[N:1]1([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[O:18][C:19]([CH3:24])=[C:20]([CH2:22]O)[N:21]=3)=[CH:13][CH:12]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.S(Cl)([Cl:27])=O>C(Cl)Cl>[Cl:27][CH2:22][C:20]1[N:21]=[C:17]([C:14]2[CH:15]=[CH:16][C:11]([CH2:10][N:1]3[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=[CH:2]3)=[CH:12][CH:13]=2)[O:18][C:19]=1[CH3:24]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 57550209{2-{4-[(1H-Benzimidazol-1-yl)methyl]phenyl}-5-methyl-1,3-oxazole-4-yl}methanol

Product 1

HCID 575502361-{4-[4-(Chloromethyl)-5-methyl-1,3-oxazol-2-yl]benzyl}-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of {2-{4-[(1H-benzimidazol-1-yl)methyl]phenyl}-5-methyl-1,3-oxazole-4-yl}methanol (0.045 g, 0.14 mmol) in CH2Cl2 was treated with a solution of thionyl chloride (0.10 mL, 1.4 mmol) in CH2Cl2 (2 mL), heated to reflux temperature, stirred for 30 min, cooled to room temperature and concentrated in vacuo. The resultant residue was partitioned between CH2Cl2 and water. The organic phase was separated, washed with water, brine, dried over Na2SO4, and evaporated to dryness under reduced pressure to give the title product, LCMS (ESI+) 337 (MH+).

Workup

  1. temperatureheated
  2. temperatureto reflux temperature
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue was partitioned between CH2Cl2 and water
  5. customThe organic phase was separated
  6. washwashed with water, brine
  7. dry with materialdried over Na2SO4
  8. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-0a38a5784f6542b89ab7bd6dfa2269cf
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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