Aniline → HCID 2797953, compound

HRID 1905464Notes

Reaction equation

HRID 1905464 reaction equation
[CH3:1][O:2][C:3]([C:5]#[C:6][C:7]([O:9][CH3:10])=[O:8])=[O:4].[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)CCl>[C:12]1([NH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:3]([O:2][CH3:1])=[O:4])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 12980Dimethyl acetylenedicarboxylate

Product 1

HCID 2797953HCID 2797953, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a stirred solution of dimethylacetylenedicarboxylate (DMAD, 0.10 mol) in 50 mL of ethylene dichloride (EDC), is slowly added a solution of aniline (0.10 mol) in 15 mL of EDC. The temperature of the reaction mixtures is maintained below 30° C. and stirring is continued for about one hour until the reaction is essentially complete. The EDC is then removed under vacuum to afford the dimethyl 3-phenylaminobut-2-ene-dioate.

Workup

  1. customThe temperature of the reaction mixtures
  2. temperatureis maintained below 30° C.
  3. customThe EDC is then removed under vacuum

Sources & evidence

ORD record
ord-5c175b57db4446ab860dc496396a8ff3
Source dataset
uspto-grants-1989_06
Patent number
US04843162

Reaction notes

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