Thionyl Chloride → HCID 13152890, compound

HRID 616611Notes

Reaction equation

HRID 616611 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][N:4]2[CH:13]=[C:14]([C:16]([OH:18])=O)[CH:15]=[C:3]12.S(Cl)([Cl:21])=O>>[Cl:21][C:16]([C:14]1[CH:15]=[C:3]2[N:4]([CH:13]=1)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:2]2=[O:1])=[O:18]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 13152888HCID 13152888, compound

Product 1

HCID 13152890HCID 13152890, compoundYield 89%

Procedure

6,11-Dihydro-11-oxo-pyrrolo[2,1-b][3]benzazepine-2-carboxylic acid (24 g., 99 mmoles) in 100 ml. of thionyl chloride was refluxed for 15 minutes. The volatiles were removed under vacuum and the residue was triturated in ether. Filtration and air-drying yielded 2-chlorocarbonyl-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepin-11-one (23 g., 89%), m.p. 147°-148.5.

Workup

  1. customThe volatiles were removed under vacuum
  2. customthe residue was triturated in ether
  3. filtrationFiltration
  4. customair-drying

Sources & evidence

ORD record
ord-1534e6471b6d45cf9487649ee0193ac0
Source dataset
uspto-grants-1978_02
Patent number
US04075225

Reaction notes

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