Dimethyl acetylenedicarboxylate → HCID 12403020, compound

HRID 1076981Notes

Reaction equation

HRID 1076981 reaction equation
CO[C:3]([C:5]#[C:6][C:7]([O:9][CH3:10])=[O:8])=[O:4].[Cl:11][C:12]1[C:17]([NH2:18])=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:19]>CO>[CH3:10][O:9][C:7]([C:6]1[NH:19][C:13]2[C:14]([C:3](=[O:4])[CH:5]=1)=[CH:15][C:16]1[C:3](=[O:4])[CH:5]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[NH:18][C:17]=1[C:12]=2[Cl:11])=[O:8]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 124029782-Chloro-m-phenylenediamine

Product 1

HCID 12403020HCID 12403020, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

11.0 g. of dimethylacetylene dicarboxylate is added dropwise to a solution of 5.25 g. of 2-chloro-1,3-diaminobenzene in 100 ml. of methanol at room temperature. The mixture is stirred for 2 hours at room temperature and the resulting yellow solid is collected by filtration. The solid is washed with 20 to 50 ml. of methanol, dried under vacuum at 60° C., and recrystallized from acetone. The tetramethyl[2-chloro-m-phenylene-diamino]dimaleate melts at 202.5°-204.5°C.

Workup

  1. customat room temperature
  2. filtrationthe resulting yellow solid is collected by filtration
  3. washThe solid is washed with 20 to 50 ml
  4. dry with materialof methanol, dried under vacuum at 60° C.
  5. customrecrystallized from acetone

Sources & evidence

ORD record
ord-26f35c171b2c40bca1487dee750bb708
Source dataset
uspto-grants-1976_05
Patent number
US03959289

Reaction notes

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