Triethylamine → HCID 22917218, compound

HRID 1973381Notes

Reaction equation

HRID 1973381 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[C:5]([NH2:10])[CH:4]=1.C(N(CC)CC)C.Br[CH:19]([C:25](OCC)=[O:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][CH:8]=1)[N:9]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:25](=[O:26])[NH:10]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69637Diethyl bromomalonateHCID 1534044-Methoxy-o-phenylenediamine

Product 1

HCID 22917218HCID 22917218, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-methoxy-o-phenylenediamine (9.5 g) and triethylamine (7 g) in ethanol (100 ml) was cooled to 0°-5° and stirred in an atmosphere of nitrogen. Diethyl bromomalonate (23.7 g) in ethaol (50 ml) was added during 30 minutes. The temperature of the mixture was maintained at 0°-5° for a further 6 hours and then allowed to rise to 20° and stirred at this temperature for 16 hours. The solid was filtered off, stirred with dilute hydrochloric acid (400 ml., 0.2N), filtered off, washed with water, dried and crystallised from a mixture of ethyl acetate and methanol, m.p. 229°.

Workup

  1. temperatureThe temperature of the mixture was maintained at 0°-5° for a further 6 hours
  2. customto rise to 20°
  3. stirringstirred at this temperature for 16 hours
  4. filtrationThe solid was filtered off
  5. stirringstirred with dilute hydrochloric acid (400 ml., 0.2N)
  6. filtrationfiltered off
  7. washwashed with water
  8. customdried
  9. customcrystallised from a mixture of ethyl acetate and methanol, m.p. 229°

Sources & evidence

ORD record
ord-3dd8cb2a00c045e0acc9946403a3ed92
Source dataset
uspto-grants-1976_12
Patent number
US03997535

Reaction notes

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