Thionyl Chloride → HCID 57550200, compound

HRID 1716838Notes

Reaction equation

HRID 1716838 reaction equation
[N:1]1([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[O:17][CH:18]=[C:19]([CH2:21]O)[N:20]=3)=[CH:12][CH:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.S(Cl)([Cl:25])=O>C(Cl)Cl>[Cl:25][CH2:21][C:19]1[N:20]=[C:16]([C:13]2[CH:14]=[CH:15][C:10]([N:1]3[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=[CH:2]3)=[CH:11][CH:12]=2)[O:17][CH:18]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 57550231HCID 57550231, compound

Product 1

HCID 57550200HCID 57550200, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of {2-[4-(1H-benzimidazol-1-yl)phenyl]-1,3-oxazol-4-yl}methanol (0.35 g, 1.2 mmol) in CH2Cl2 was cooled to 0° C., treated with a solution of thionyl chloride (0.37 g, 3.0 mmol) in CH2Cl2, stirred at 0° C. for 3 h and concentrated in vacuo. The resultant residue was partitioned between CH2Cl2 and water. The organic phase was separated, washed sequentially with water and brine, dried over Na2SO4 and evaporated to dryness under reduced pressure to afford the title product, 1HNMR (CDCl3, 400 MHz): 8.25 (d, J=8.4 Hz, 2H), 8.17 (s, 2H), 7.67 (d, J=8.0 Hz, 1H), 7.60 (d, J=5.6 Hz, 1H), 7.36-7.38 (m, 3H), 7.26 (s, 1H), 4.61 (s, 2H). LCMS (ESI+) 310 (MH+).

Workup

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

Sources & evidence

ORD record
ord-72782fdd403d4c1b8d3d27caa47619a7
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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