Ethanolamine → HCID 3478878, compound

HRID 1413339Notes

Reaction equation

HRID 1413339 reaction equation
OCC[C:4]1[C:5]([N+:15]([O-:17])=[O:16])=[C:6]2[C:11](=[O:12])[NH:10][C:8](=[O:9])[C:7]2=[CH:13][CH:14]=1.[N+](C1C=CC=[C:23]2[C:24](OC(=O)C=12)=[O:25])([O-])=O.C(CN)O.OCCN1C(=O)C2=C(N=[N+]=[N-])C=CC=C2C1=O>C1(C)C=CC=CC=1.CN(C)C=O>[OH:25][CH2:24][CH2:23][N:10]1[C:11](=[O:12])[C:6]2=[C:5]([N+:15]([O-:17])=[O:16])[CH:4]=[CH:14][CH:13]=[C:7]2[C:8]1=[O:9]

Participants

7

Reactant 4

HCID 700EthanolamineHCID 216313-Nitrophthalic anhydrideHCID 20291885HCID 20291885, compoundHCID 86737472HCID 86737472, compound

Product 1

HCID 3478878HCID 3478878, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

N-(β-Hydroxyethyl-3-nitrophthalimide, used in the above example, can be prepared as follows: a mixture of 19.3 g (0.1 mol) of 3-nitrophthalic anhydride, 6.7 g (0.1 mol) of ethanolamine, 50 ml of N,N-dimethylformamide (DMF) and 30 ml of toluene is boiled, the water formed in the course of the reaction being removed azeotropically. The reaction mixture is then evaporated to dryness. The residue is dissolved in 200 ml of methylene chloride and the solution is extracted by shaking with 100 ml of saturated sodium chloride solution. The methylene chloride solution is then dried with anhydrous sodium sulphate and evaporated. 18 g (76% of theory) of N-(β-hydroxyethyl)-3-nitrophthalimide are obtained as an oily residue, which crystallises in a short time; melting point 93° C. IR spectrum (CH2Cl2): 1790 cm-1 and 1730 cm-1 (CO--N--CO); 1550 cm-1 and 1370 cm-1 (CO2).

Workup

  1. customcan be prepared
  2. custombeing removed azeotropically
  3. customThe reaction mixture is then evaporated to dryness
  4. dissolutionThe residue is dissolved in 200 ml of methylene chloride
  5. extractionthe solution is extracted
  6. dry with materialThe methylene chloride solution is then dried with anhydrous sodium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-037d612b3a9b4674b686f7961822aae3
Source dataset
uspto-grants-1981_02
Patent number
US04250096

Reaction notes

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