Ammonia → HCID 178513677, compound

HRID 1577864Notes

Reaction equation

HRID 1577864 reaction equation
[NH3:1].Br[CH2:3][CH2:4][N:5]=[C:6]([OH:22])[C:7]1[C:8](=[CH:12][C:13](=[C:17]([CH:21]=1)[C:18](=[NH:20])[OH:19])[C:14]([OH:16])=[O:15])[C:9]([OH:11])=[O:10]>CN(C)C=O>[NH2:1][CH2:3][CH2:4][N:5]=[C:6]([OH:22])[C:7]1[C:8](=[CH:12][C:13](=[C:17]([CH:21]=1)[C:18](=[NH:20])[OH:19])[C:14]([OH:16])=[O:15])[C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 178513676HCID 178513676, compound

Product 1

HCID 178513677HCID 178513677, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

To a stirred solution of liquid ammonia, 22 ml. (1.0 mole), in 200 ml. of dimethylformamide is added portionwise 3.2 g. (10 mmole) of N-(2-bromoethyl)pyromellitic diimide. The mixture is stirred at room temperature (23° C.) for 48 hours. Excess ammonia is removed by concentration under reduced pressure without heating. Several volumes of dilute aqueous sodium carbonate are added to the concentrate with ice bath cooling. The insolubles are collected, rinsed with water, cold methanol, and ethyl ether furnishing N-(2-aminoethyl)pyromellitic diimide.

Workup

  1. customExcess ammonia is removed by concentration under reduced pressure
  2. temperaturewithout heating
  3. additionSeveral volumes of dilute aqueous sodium carbonate are added to the
  4. concentrationconcentrate with ice bath
  5. temperaturecooling
  6. customThe insolubles are collected
  7. washrinsed with water, cold methanol, and ethyl ether

Sources & evidence

ORD record
ord-e2f5196259754181a45953ae0d639094
Source dataset
uspto-grants-1981_09
Patent number
US04289784

Reaction notes

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