Hydrochloric Acid → HCID 178478961, compound

HRID 1518124Notes

Reaction equation

HRID 1518124 reaction equation
[Cl:1][C:2]1[C:7]2[NH:8][C:9]([C:11]3[CH2:15][C:14]4([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]4)[O:13][N:12]=3)=[N:10][C:6]=2[CH:5]=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([F:30])([F:29])[F:28])[CH:3]=1.Cl>CCOC(C)=O>[ClH:1].[Cl:1][C:2]1[C:7]2[NH:8][C:9]([C:11]3[CH2:15][C:14]4([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]4)[O:13][N:12]=3)=[N:10][C:6]=2[CH:5]=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([F:30])([F:29])[F:28])[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178506132HCID 178506132, compound

Product 1

HCID 178478961HCID 178478961, compoundYield 187.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-[7-Chloro-5-(2-trifluoromethylphenyl)-1H-benzimidazol-2-yl]-1-oxa-2-aza-spiro[4.5]dec-2-ene (2.39 g, 5.52 mmol) was placed in a 100 mL round-bottom flask. EtOAc (10 mL) was added, and the solid was allowed to dissolve. HCl (5.52 mL, 5.52 mmol, 1 M in ether) was added dropwise via syringe with swirling to ensure sufficient mixing. The mixture was sonicated for 2 min, resulting in a white precipitate, which was isolated by filtration and washed twice with EtOAc (10 mL) then once with ether (20 mL). The solid was dried under high vacuum, yielding the title compound (2.43 g, 94%). 1H-NMR (400 MHz, d6-DMSO) δ: 7.86 (d, J=7.8 Hz, 1H), 7.75 (t, J=7.5 Hz, 1H), 7.65 (t, J=7.6 Hz, 1H), 7.51 (d, J=7.6 Hz, 1H), 7.38 (s, 1H), 7.26 (s, 1H), 3.33 (s, 2H), 1.63-1.81 (m, 6H), 1.32-1.58 (m, 4H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C22H19ClF3N3O: 434.1 (M+H). found: 434.4.

Workup

  1. dissolutionto dissolve
  2. customThe mixture was sonicated for 2 min
  3. customresulting in a white precipitate
  4. customwhich was isolated by filtration
  5. washwashed twice with EtOAc (10 mL)
  6. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-82510b6dc3d24fdfabd572a64845bdfa
Source dataset
uspto-grants-2012_07
Patent number
US08232409B2

Reaction notes

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