Hydrochloric Acid → HCID 57024939, compound

HRID 973806Notes

Reaction equation

HRID 973806 reaction equation
[C:1]([C:3]1[CH:14]=[CH:13][C:6]([CH:7]=[CH:8][C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1)#[N:2].[ClH:15].[Cl:16][C:17]([Cl:21])([Cl:20])[C:18]#[N:19]>[Br-].[Al+3].[Br-].[Br-].ClCCl>[Cl:16][C:17]([Cl:21])([Cl:20])[C:18]1[N:19]=[C:18]([C:17]([Cl:20])([Cl:16])[Cl:15])[N:19]=[C:1]([C:3]2[CH:14]=[CH:13][C:6]([CH:7]=[CH:8][C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=2)[N:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 11011TrichloroacetonitrileHCID 53412322HCID 53412322, compound

Product 1

HCID 57024939HCID 57024939, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 166749BromhydrolSolvent

Conditions

Temperature
28 °C

Procedure

Methyl 4-cyanocinnamate (46 pw) is suspended in the absence of moisture and at 24 to 28° C. in a mixture of trichloroacetonitrile (208.2 pw) and aluminum bromide (7.68 pw). The mixture is stirred, and hydrogen chloride is introduced at constant temperature. Temporarily, an almost clear solution is formed, but soon thereafter the mixture becomes syrup-like. Introduction of hydrogen chloride gas is stopped after 4 hours, stirring is discontinued and the mixture is maintained at 28° C. for 12 hours. The resulting solid material is dissolved in 500 pw of dichloromethane and washed twice with 250 pw of water. The organic phase is dried over calcium chloride, and the solvent is evaporated. The residue is recrystallized from a 1:1 mixture of methanol and 2-methoxyethanol.

Workup

  1. customTemporarily, an almost clear solution is formed
  2. stirringstirring
  3. washwashed twice with 250 pw of water
  4. dry with materialThe organic phase is dried over calcium chloride
  5. customthe solvent is evaporated
  6. customThe residue is recrystallized from a 1:1 mixture of methanol and 2-methoxyethanol

Sources & evidence

ORD record
ord-eb23115a90304b58a0223317b95175e2
Source dataset
uspto-grants-1991_11
Patent number
US05064959

Reaction notes

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