Hydrochloric Acid → HCID 9996568, compound

HRID 1607492Notes

Reaction equation

HRID 1607492 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 (11.3g) 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-09586728f4af47648ddb0ee0aff54916
Source dataset
uspto-grants-1989_09
Patent number
US04865764

Reaction notes

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