Formamide → HCID 22379917, compound

HRID 1988770Notes

Reaction equation

HRID 1988770 reaction equation
[Br:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]([CH2:20][CH3:21])[C:7]([CH2:9][CH2:10][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)=O)=[N:8][C:4]=2[CH:3]=1.BrBr.[CH:26]([NH2:28])=[S:27].C(N)=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=S>O1CCOCC1>[Br:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]([CH2:20][CH3:21])[C:7]([CH2:9][C:10]3[S:27][CH:26]=[N:28][C:11]=3[C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)=[N:8][C:4]=2[CH:3]=1

Participants

7

Reactant 5

HCID 713FormamideHCID 14817Phosphorus sulfide (P2S5)HCID 24408BromineHCID 3005587MethanethioamideHCID 22379891HCID 22379891, compound

Product 1

HCID 22379917HCID 22379917, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of 3-(5-bromo-1-ethyl-1H-benzoimidazol-2-yl)-1-(3-fluoro-phenyl)-propan-1-one (0.2 g, 0.53 mmol) and bromine (0.1 g, 0.62 mmol) is refluxed in 1,4-dioxane for 2 hours. Thioformamide (freshly made from formamide and P2S5 in 1,4-dioxane) (1.3 mmol) are added to the solution. The mixture is refluxed overnight. The solvent is removed and NaHCO3 (aq.) (15 mL) and DCM (40 mL) are added to the residue. The organic layer is separated and the aqueous layer is extracted with DCM (2×30 mL). The combined organic layers are dried and solvent removed. The crude is purified by PTLC (5% methanol in DCM) to give 5-bromo-1-ethyl-2-[4-(3-fluoro-phenyl)-thiazol-5-ylmethyl]-1H-benzoimidazole. 1H NMR (CDCl3) δ 8.78 (s, 1H), 7.91 (s, 1H), 7.38-7.48 (m, 4H), 7.11-7.19 (m, 2H), 4.59 (s, 2H), 3.90 (q, 2H), 1.12 (t, 3H).

Workup

  1. additionare added to the solution
  2. temperatureThe mixture is refluxed overnight
  3. customThe solvent is removed
  4. additionNaHCO3 (aq.) (15 mL) and DCM (40 mL) are added to the residue
  5. customThe organic layer is separated
  6. extractionthe aqueous layer is extracted with DCM (2×30 mL)
  7. customThe combined organic layers are dried
  8. customsolvent removed
  9. customThe crude is purified by PTLC (5% methanol in DCM)

Sources & evidence

ORD record
ord-ceada19085834e36b7912785d99fcf01
Source dataset
uspto-grants-2010_01
Patent number
US07642267B2

Reaction notes

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