2,6-Dimethylaniline → HCID 53800639, compound

HRID 66152Notes

Reaction equation

HRID 66152 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[C:5]([C:7](=[CH2:11])C(O)=O)=[O:6].[NH2:16][C:17]1[C:18]([CH3:24])=[CH:19][CH:20]=[CH:21][C:22]=1[CH3:23].O=P(Cl)(Cl)Cl.C(N(CC)CC)C.[O:37]1CCC[CH2:38]1>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[C:5]([CH:7]=[CH:11][C:38]([NH:16][C:17]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:24])=[O:37])=[O:6]

Participants

7

Reactant 5

HCID 68962,6-DimethylanilineHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 227558013,4-Dichlorobenzoylacrylic acid

Product 1

HCID 53800639HCID 53800639, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 6.12 g. (0.025 moles) of 3,4-dichlorobenzoylacrylic acid and 4.0 ml. (3.94 g., 0.0325 moles) of 2,6-xylidine in 125 ml. of tetrahydrofuran is cooled to 5° C. and treated in succession with 3.0 ml. (5 g., 0.0328 moles) of POCl3 and 10 ml. (7.25 g., 0.072 moles) of triethylamine. The temperature rises to 25° C. and then falls to 20° C. After stirring for one hour, the suspension mixture is diluted with water and stripped of solvent. A semi-crystalline solid is obtained which is washed with water, then slurried with ethyl acetate. After filtering and washing with ether, 2.8 g. of 3-(3,4-dichlorobenzoyl)-2',6'-dimethylacrylanilide is obtained having a melting point of 213° C.-215° C.

Workup

  1. additiontreated in succession with 3.0 ml
  2. customrises to 25° C.
  3. customfalls to 20° C
  4. customA semi-crystalline solid is obtained which
  5. washis washed with water
  6. filtrationAfter filtering
  7. washwashing with ether, 2.8 g

Sources & evidence

ORD record
ord-d752e7f3f2404551b2b20e5b7c21fd71
Source dataset
uspto-grants-1978_12
Patent number
US04130661

Reaction notes

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