Hydrochloric Acid → HCID 9996568, compound

HRID 414707Notes

Reaction equation

HRID 414707 reaction equation
[Cl:1][CH2:2][C:3]#N.Cl.[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[N:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.C([O:27]CC)C>[Cl-].[Cl-].[Zn+2]>[Cl:1][CH2:2][C:3]([C:15]1[N:14]([CH:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[F:6])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:18]=[CH:17][CH:16]=1)=[O:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 7856ChloroacetonitrileHCID 10354786HCID 10354786, compound

Product 1

HCID 9996568HCID 9996568, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
95 °C

Procedure

A cooled mixture of chloroacetonitrile (11.3 g) and ZnCl2 (10.2 g) in 10 ml of diethyl ether was saturated with gaseous hydrochloric acid. A solution of 1-[(2-fluorophenyl)phenylmethyl]pyrrole (18.8 g) in 200 ml of ethyl ether was added and this was stirred for 6 hours. The resulting solid was collected, added to water and heated at 95° C. for 2 hours. This was then cooled and extracted with ethyl ether and the organics were dried (saturated NaCl, MgSO4) and concentrated to give 20.4 g of a yellow oil, a portion of which was crystallized to give a white solid, mp 86°-91° C.

Workup

  1. customThe resulting solid was collected
  2. additionadded to water
  3. temperatureThis was then cooled
  4. extractionextracted with ethyl ether
  5. dry with materialthe organics were dried (saturated NaCl, MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f52791c626d344659897eba5024f52fc
Source dataset
uspto-grants-1988_12
Patent number
US04794110

Reaction notes

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