O-Phenylenediamine → HCID 22257852, compound

HRID 2083985Notes

Reaction equation

HRID 2083985 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][CH2:3][C:2]1=O.[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH2:15]>C1(C)C=C(C)C=C(C)C=1>[OH:1][CH2:6][CH2:5][O:4][CH2:3][C:2]1[NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:15]=1

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 18233Dioxanone

Product 1

HCID 22257852HCID 22257852, compound

Reagents, catalysts & solvents 1

HCID 7947MesityleneSolvent

Procedure

Using a Dean-Stark separator, 1.4-dioxan-2-one (204 g, 20 mmol) and 1.2-diaminobenzene (2.16 g, 20 mmol) were heated under reflux in mesitylene (150 ml) for 10 h. The crystals formed on cooling were then filtered off with suction (2.94 g. 77% of theory). Rf (dichloromethane:methanol 10:1)=0.45, MS (EI)=192 (M+, 20%), 148 (20%), 147 (40%), 132 (100%), 1H-NMR (DMSO-d6): 3.6 (4H, s); 4.65 (1H, s); 4.7 (2H, s); 7.1-7.2 (2H, m); 7.45 (1H, d); 7.55 (1H, d); 12.4 (1H, br s).

Workup

  1. temperaturewere heated
  2. customThe crystals formed
  3. temperatureon cooling
  4. filtrationwere then filtered off with suction (2.94 g. 77% of theory)

Sources & evidence

ORD record
ord-59d48bb1b96b47a2b0bbf49e2c8555fa
Source dataset
uspto-grants-2004_04
Patent number
US06716849B1

Reaction notes

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