1,2-Dichloroethane → HCID 20147792, compound

HRID 1982286Notes

Reaction equation

HRID 1982286 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][N:9]([CH3:29])[C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[C:25]3[C:20](=[CH:21][C:22]([N:26]([CH3:28])[CH3:27])=[CH:23][CH:24]=3)[C:18](=[O:19])[O:17]2)=[CH:12][CH:11]=1.[CH3:30][N:31]1C=CC=[CH:32]1.[Cl-].[Al+3].[Cl-].[Cl-].[CH2:40](Cl)CCl>O>[CH3:40][C:2]1[CH:7]=[C:6]([N:31]([CH3:32])[CH3:30])[CH:5]=[CH:4][C:3]=1[CH:16]([C:25]1[CH:24]=[CH:23][C:22]([N:26]([CH3:28])[CH3:27])=[CH:21][C:20]=1[C:18]([OH:17])=[O:19])[C:13]1[CH:14]=[CH:15][C:10]([N:9]([CH3:29])[CH3:8])=[CH:11][CH:12]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 73041-MethylpyrroleHCID 7964ChlorobenzeneHCID 936931(3H)-Isobenzofuranone, 6-(dimethylamino)-3-[4-(dimethylamino)phenyl]-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 20147792HCID 20147792, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 75.0 ml of monochlorobenzene, 7.4 g of 3-(4-dimethylaminophenyl)-6-dimethylaminophthalide and 2.2 g of N-methylpyrrole maintained at 0°-5° C. by means of an external ice-bath, there was slowly added 6.65 g of anhydrous aluminum chloride. After stirring for approximately three hours, there was slowly added with continued cooling at 0°-5° C., 100 ml of water and 100 ml of ethylene dichloride. The layers were separated and the organic layer extracted with 150 ml of fresh water. The organic layer was then extracted with 100 ml of 3N hydrochloric acid, separated and the pH of this aqueous acid layer adjusted to 4.5 with five percent aqueous sodium hydroxide solution. The green solid which had formed was collected by filtration. After reslurrying in a mixture of acetone and methanol, the solid was filtered and dried to obtain 5.2 g of 2-[α-(4-dimethylaminophenyl)-α-(1-methyl-2-pyrrolyl)]methyl-5-dimethylaminobenzoic acid (Formula III: R=CH3 ; X=H; Y=4-(CH3)2 --NC6H4 ; Z=1-CH3 -2-pyrrolyl).

Workup

  1. temperaturemaintained at 0°-5° C. by means of an external ice-bath
  2. additionthere was slowly added
  3. temperaturewith continued cooling at 0°-5° C.
  4. customThe layers were separated
  5. extractionthe organic layer extracted with 150 ml of fresh water
  6. extractionThe organic layer was then extracted with 100 ml of 3N hydrochloric acid
  7. customseparated
  8. customThe green solid which had formed
  9. filtrationwas collected by filtration
  10. additionAfter reslurrying in a mixture of acetone and methanol
  11. filtrationthe solid was filtered
  12. customdried

Sources & evidence

ORD record
ord-2dad97f33d5e44f7ad13aad5b8239a55
Source dataset
uspto-grants-1986_06
Patent number
US04595768

Reaction notes

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