Maleic Anhydride → 135861-52-8

HRID 982155Notes

Reaction equation

HRID 982155 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[NH2:8][C:9]1[CH:10]=[C:11]([Sn:15]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19])[CH:12]=[CH:13][CH:14]=1>C1(C)C=CC=CC=1>[CH2:24]([Sn:15]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:20][CH2:21][CH2:22][CH3:23])[C:11]1[CH:10]=[C:9]([NH:8][C:1](=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5])[CH:14]=[CH:13][CH:12]=1)[CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 9907970Benzenamine, 3-(tributylstannyl)-

Product 1

HCID 67938515135861-52-8

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Maleic anhydride (0.18 g, 1.8 mmol) was dissolved in toluene (2 mL). m-Aminophenyltributylstannane as described above (0.70 g, 1.8 mmol) in toluene (4 mL) was added dropwise over a 5 minute period. After the addition was complete, the reaction mixture was stirred for 15 minutes at room temperature then cooled in an ice-water bath. The precipitaed yellow product N-(m-tri-n-butylstannylphenyl)maleamic acid was collected by vacuum filtration, recrystallized from toluene and dried overnight in a vacuum dessicator (0.75 g, 85%): mp. 130°-131° C. 1H NMR (Me2SO-d6, δ); 10.4 (singlet, 1H, OH); 7.6 (singlet, 2H, aryl C2-H and aryl C6-H); 7.3 (triplet, 1H, aryl C5-H); 7.2 (doublet, 1H, aryl C4-H); 6.4 (doublet of doublets, 2H AB, J=12 Hz, 2 CHC=O); 0.9-1.6 (muliplets, 27H, 3× n-C4H9).

Workup

  1. additionwas added dropwise over a 5 minute period
  2. additionAfter the addition
  3. temperaturethen cooled in an ice-water bath
  4. filtrationThe precipitaed yellow product N-(m-tri-n-butylstannylphenyl)maleamic acid was collected by vacuum filtration
  5. customrecrystallized from toluene
  6. customdried overnight in a vacuum dessicator (0.75 g, 85%)

Sources & evidence

ORD record
ord-9b87114a29ee4abb900beb5f2ae51d14
Source dataset
uspto-grants-1991_02
Patent number
US04994557

Reaction notes

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