Diethyl Ether → Benzaldehyde, 2,2'-iminobis-

HRID 2185086Notes

Reaction equation

HRID 2185086 reaction equation
[NH:1]([C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](O)=[O:14])[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C1COCC1.[H-].CN1CCN([Al+]N2CCN(C)CC2)CC1.C(OCC)C>O>[NH:1]([C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[CH:13]=[O:14])[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8028Tetrahydrofuran2×HCID 11371Diphenylamine-2,2'-dicarboxylic acidHCID 22248554Bis(1-methylpiperazine-4-yl)aluminum hydride

Product 1

HCID 148482Benzaldehyde, 2,2'-iminobis-Yield 33.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-20 °C

Procedure

To a 500-ml reactor thoroughly dried and purged with argon, 2.3 g (8.94 mmol) of 2,2′-iminodibenzoic acid and 50 ml of THF were introduced, and they were cooled to −20° C. At that temperature, 90 ml of a THF solution (0.3 M) of bis(1-methylpiperazine-4-yl)aluminum hydride was dropwise added with stirring. Then, the temperature of the system was raised, and the reaction was conducted for 24 hours under reflux. The reaction solution was allowed to stand for cooling to room temperature. To the solution, 100 ml of diethyl ether was added, and 150 ml of water was further added slowly with ice cooling. The oil layer obtained by phase separation was concentrated and subjected to isolation by means of silica gel column chromatography to obtain 673 mg of 2,2′-iminodibenzaldehyde. To a 100-ml reactor thoroughly dried and purged with argon, 650 mg (2.89 mmol) of the 2,2′-iminodibenzaldehyde, 699 mg (5.77 mmol) of 2,6-dimethylaniline, 50 ml of dehydrated methanol and 0.2 ml of acetic acid were introduced, and they were reacted at room temperature for 12 hours. From the reaction solution, the solvent was distilled off, and the remainder was subjected to isolation by means of silica gel column chromatography to obtain 237 mg (yield: 6.1%) of a compound represented by the following formula (L6).

Workup

  1. customTo a 500-ml reactor thoroughly dried
  2. additionwere introduced
  3. temperatureThen, the temperature of the system was raised
  4. temperatureunder reflux
  5. temperaturefor cooling to room temperature
  6. customThe oil layer obtained by phase separation
  7. concentrationwas concentrated

Sources & evidence

ORD record
ord-b742dba322d34badb96a49591577b459
Source dataset
uspto-grants-2002_06
Patent number
US06399724B1

Reaction notes

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