Maleic Anhydride → HCID 14473346, compound

HRID 1607375Notes

Reaction equation

HRID 1607375 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH2:8]([O:10][CH:11]([O:16][CH2:17][CH3:18])[CH2:12][CH2:13][CH2:14][NH2:15])[CH3:9]>C(Cl)Cl>[CH2:17]([O:16][CH:11]([O:10][CH2:8][CH3:9])[CH2:12][CH2:13][CH2:14][NH:15][C:4](=[O:5])/[CH:3]=[CH:2]\[C:1]([OH:6])=[O:7])[CH3:18]

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 806724,4-Diethoxybutylamine2×

Product 1

HCID 14473346HCID 14473346, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Maleic anhydride (85 g) in 1300 mL of CH2Cl2 was cooled to 15° C. and treated with 155 g of 4-aminobutyraldehyde diethyl acetal (AmBDA). (Other preparations used the reverse mode of addition with similar results.) Fifteen min after the addition was complete no further AmBDA was detected by glpc. The solvent was removed under reduced pressure (maintained at 0.2 torr for 2 h to assure completion) to give 230 g of slightly orange colored thick oil. On standing for several months at 0° C., this material solidified to an off-white solid.

Workup

  1. additionthe reverse mode of addition with similar results
  2. addition) Fifteen min after the addition
  3. customThe solvent was removed under reduced pressure (maintained at 0.2 torr for 2 h to assure completion)
  4. customto give 230 g of slightly orange colored thick oil
  5. waitOn standing for several months at 0° C.

Sources & evidence

ORD record
ord-fa9b136a66db4043aaf168ea2444c39e
Source dataset
uspto-grants-1989_09
Patent number
US04864055

Reaction notes

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