O-Phenylenediamine → HCID 797102, compound

HRID 1175650Notes

Reaction equation

HRID 1175650 reaction equation
[CH2:1]([N:4]([CH2:11][C:12](OCC)=O)[CH2:5][C:6](OCC)=O)[CH:2]=[CH2:3].[C:17]1([NH2:24])[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH2:23]>>[NH:23]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:24]=[C:12]1[CH2:11][N:4]([CH2:5][C:6]1[NH:24][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:23]=1)[CH2:1][CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 7243O-PhenylenediamineHCID 59559133HCID 59559133, compound

Product 1

HCID 797102HCID 797102, compound

Conditions

Temperature
190 °C

Procedure

A mixture of 7.3 g (32.0 mmol) diethyl N-allyliminodiacetate and 6.9 g (64 mmol) o-phenylene diamine was stirred at 190° C. for 4 hour and the formed volatile materials were distilled off. The reaction mixture was then left to cool down to room temperature and acetone (100 ml) was added. The mixture was sonicated for 10 minutes, the formed residue filtered, washed with 2×5 ml acetone and dried under vacuum. Yield—4.5 g (44.0%). 1H NMR (250 MHz, CDCl3□, ppm: 3.22 (d, 2H), 3.95 (m, 4H), 5.20 (m, 2H), 5.90 (m, 1H), 7.15 (m, 4H), 7.53 (m, 4H), 12.11 (br.s 2H).

Workup

  1. distillationthe formed volatile materials were distilled off
  2. waitThe reaction mixture was then left
  3. temperatureto cool down to room temperature
  4. additionacetone (100 ml) was added
  5. customThe mixture was sonicated for 10 minutes
  6. filtrationthe formed residue filtered
  7. washwashed with 2×5 ml acetone
  8. customdried under vacuum

Sources & evidence

ORD record
ord-a1590bf763d249daa7a5797736d2eba9
Source dataset
uspto-grants-2010_11
Patent number
US07842638B2

Reaction notes

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