Phosphorus oxychloride → HCID 178478315, compound

HRID 496250Notes

Reaction equation

HRID 496250 reaction equation
[I:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7](=O)[NH:8][C:4]=2[CH:3]=1.O=P(Cl)(Cl)[Cl:14]>[Cl-].C[N+](C)(C)C>[Cl:14][C:7]1[NH:6][C:5]2[CH:10]=[CH:11][C:2]([I:1])=[CH:3][C:4]=2[N:8]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 120716615-IODO-1,3-DIHYDRO-BENZIMIDAZOL-2-ONE

Product 1

HCID 178478315HCID 178478315, compound

Reagents, catalysts & solvents 1

HCID 6379Tetramethylammonium chlorideCatalyst

Procedure

Heat a solution of 5-iodo-1,3-dihydro-benzimidazol-2-one (6.50 g, 25.0 mmol; Feitelson et al. (1952) J. Chem. Soc. 2389) and tetramethylammonium chloride (1.37 g, 12.5 mmol) to 100° C. in POCl3 (10 mL) for 18 hours. After cooling, remove the excess POCl3 in vacuo, and triturate the residue in ice-water (200 mL). After stirring for 30 minutes, filter the precipitate to obtain 2-chloro-5-iodo-1H-benzimidazole as a gray solid. B. 1′-(5-iodo-1H-benzimidazol-2-yl)-spiro[isobenzofuran-1,4′-piperidin]-3-one

Workup

  1. temperatureAfter cooling
  2. customremove the excess POCl3 in vacuo
  3. customtriturate the residue in ice-water (200 mL)
  4. filtrationfilter the precipitate

Sources & evidence

ORD record
ord-d9066c7c4bfe4354abccea5354d02080
Source dataset
uspto-grants-2005_09
Patent number
US06943199B2

Reaction notes

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