Phosphorus oxychloride → HCID 12519146, compound

HRID 2052705Notes

Reaction equation

HRID 2052705 reaction equation
[C:1]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]1[C:24]2[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=2)[CH2:18][CH2:17]1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)Cl>C(Cl)Cl>[ClH:25].[Cl:25][C:21]1[CH:20]=[C:19]2[C:24]3=[C:23]([CH:22]=1)[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[N:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]3[CH2:17][CH2:18]2

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 12519131HCID 12519131, compound

Product 1

HCID 12519146HCID 12519146, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An ice cold solution of 43.48 g of 1-(2-benzamidophenyl)-5-chloroindoline in 150 ml CH2Cl2 is treated dropwise over 80 minutes with 215 ml POCl3. At the end of the addition, the reaction mixture is permitted to warm to room temperature and the solvent (CH2Cl2) is distilled off at ambient pressure. The resulting POCl3 solution is heated at reflux for 5 hours and then permitted to cool under N2 to room temperature and stand overnight. The POCl3 is distilled off at aspirator pressure. The resulting crude salt is treated cautiously with absolute ethanol and then boiled. The product is filtered, washed with 1:1 ethanol-ether, then with dry ether and is suction dried. Recrystallization from hot ethanol affords 4-chloro-1,2-dihydro-6-phenylindolo[1,7-ab][1,5]benzodiazepine hydrochloride, m.p. 231° C. dec.

Workup

  1. additionAt the end of the addition
  2. distillationthe solvent (CH2Cl2) is distilled off at ambient pressure
  3. temperatureThe resulting POCl3 solution is heated
  4. temperatureat reflux for 5 hours
  5. temperatureto cool under N2 to room temperature
  6. distillationThe POCl3 is distilled off at aspirator pressure
  7. additionThe resulting crude salt is treated cautiously with absolute ethanol
  8. filtrationThe product is filtered
  9. washwashed with 1:1 ethanol-ether
  10. customdried
  11. customRecrystallization from hot ethanol

Sources & evidence

ORD record
ord-cd2258453de64e0b87462cba786ccd44
Source dataset
uspto-grants-1980_01
Patent number
US04186199

Reaction notes

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