Phosphorus oxychloride → 10-chloro-6,7,8,9-tetrahydro-5H-1,4,10a-triaza-cyclohepta[f]indene

HRID 2251103Notes

Reaction equation

HRID 2251103 reaction equation
[N:1]1[N:9]2[C:4]([N:5]=[C:6]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:7]3=[C:8]2O)=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:18])=O.C(N(C(C)C)CC)(C)C>C1(C)C=CC=CC=1>[Cl:18][C:8]1[N:9]2[C:4]([N:5]=[C:6]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:7]=13)=[CH:3][CH:2]=[N:1]2

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 178515163HCID 178515163, compound

Product 1

HCID 5858769810-chloro-6,7,8,9-tetrahydro-5H-1,4,10a-triaza-cyclohepta[f]indeneYield 42.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 6,7,8,9-tetrahydro-5H-1,4,10a-triaza-cyclohepta[f]inden-10-ol (5 g, 29.4 mmol) in toluene (20 mL) was added phosphorus oxychloride (37 g, 246 mmol) and diisopropylethylamine (3.1 g, 24.6 mmol). The mixture was heated to reflux for 40 min then cooled to room temperature. The product crystallized from the reaction mixture on standing over a two-day period at room temperature. The solid was collected and washed with ether to give 10-chloro-6,7,8,9-tetrahydro-5H-1,4,10a-triaza-cyclohepta[f]indene (2.3 g, 42.5% yield). The product was used without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 40 min
  3. customThe product crystallized from the reaction mixture
  4. waiton standing over a two-day period at room temperature
  5. customThe solid was collected
  6. washwashed with ether

Sources & evidence

ORD record
ord-4807f92469964a52aea961165b59b931
Source dataset
uspto-grants-2008_01
Patent number
US07319103B2

Reaction notes

Loading…