Acetic Anhydride → HCID 54573772, compound

HRID 1382839Notes

Reaction equation

HRID 1382839 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=O)C.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:20][CH:19]=2)=[CH2:17])=[CH:12][CH:11]=1.[Cl:29][C:30]1[C:31]([Cl:43])=[C:32]([Cl:42])[C:33]([Cl:41])=[C:34]2[C:39](=O)[O:38][C:36](=[O:37])[C:35]=12.[OH-].[Na+]>O.ClC1C=CC=CC=1Cl>[N:24]1([C:21]2[CH:22]=[CH:23][C:18]([C:16]([C:13]3[CH:14]=[CH:15][C:10]([O:9][CH3:8])=[CH:11][CH:12]=3)=[CH:17][C:39]3([CH:17]=[C:16]([C:13]4[CH:14]=[CH:6][C:5]([O:4][CH3:1])=[CH:11][CH:12]=4)[C:18]4[CH:23]=[CH:22][C:21]([N:24]5[CH2:28][CH2:27][CH2:26][CH2:25]5)=[CH:20][CH:19]=4)[C:34]4[C:35](=[C:30]([Cl:29])[C:31]([Cl:43])=[C:32]([Cl:42])[C:33]=4[Cl:41])[C:36](=[O:37])[O:38]3)=[CH:19][CH:20]=2)[CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8326Tetrachlorophthalic anhydrideHCID 14798Sodium HydroxideHCID 143237921-{4-[1-(4-Methoxyphenyl)ethenyl]phenyl}pyrrolidine

Product 1

HCID 54573772HCID 54573772, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
120 °C

Procedure

Into a mixture of 25 ml of acetic anhydride and 75 ml of o-dichlorobenzene, 14.0 g of 1-(p-methoxyphenyl)-1-(p-pyrrolidinophenyl)ethylene (m.p. 115°-118° C.) and 21.5 g of tetrachlorophthalic anhydride were added and the mixture was stirred for 6 hours at 120° C. Into 200 ml of water the reaction mixture was added and after making the mixture alkaline by adding sodium hydroxide, the alkaline reaction mixture was extracted with 70 ml of toluene. The solid matter obtained by evaporating toluene from the extract was recrystallized from acetone while purifying with activated carbon to obtain 17.6 g of pale yellow crystals melting at 159° to 161° C. (Yield: 85.2%)

Workup

  1. additionwere added
  2. customthe alkaline reaction mixture
  3. extractionwas extracted with 70 ml of toluene
  4. customThe solid matter obtained
  5. customby evaporating toluene from the extract
  6. customwas recrystallized from acetone
  7. customwhile purifying with activated carbon

Sources & evidence

ORD record
ord-69037fed5edf4976bc7054704dc7f054
Source dataset
uspto-grants-1989_02
Patent number
US04808567

Reaction notes

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