4-Nitro-1,2-phenylenediamine → HCID 838516, compound

HRID 2256400Notes

Reaction equation

HRID 2256400 reaction equation
Cl.C(O[C:5](=N)[CH2:6][CH2:7][CH3:8])C.[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([NH2:20])[CH:14]=1)([O-:12])=[O:11]>C(O)C>[CH2:6]([C:5]1[NH:20][C:15]2[CH:14]=[C:13]([N+:10]([O-:12])=[O:11])[CH:18]=[CH:17][C:16]=2[N:19]=1)[CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 51117914-Nitro-1,2-phenylenediamineHCID 12235055Ethyl butyrimidate hydrochloride

Product 1

HCID 838516HCID 838516, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl-butyroimidate hydrochloride (7.6 g, 50 mmol) and 4-nitro-1,2-phenylenediamine (7.6 g, 50 mmol) in ethanol (100 mL) was refluxed for 18 hours. The ethanol was evaporated under vacuum. The sticky solid was suspended in H2O (100 mL). Separation of the yellow solid gave the title compound (5.3 g, 52% yield). 1H-NMR (DMSO-d6 ; 200 MHz) δ 12.9 (s, 1H), 8.4 (s, 1H), 8.0-8.05 (d, 1H), 7.6-7.64 (d, 1H), 2.8-2.85 (t, 2H), 1.7-1.85 (m, 2H), 0.9-1.0 ppm (t, 3H),

Workup

  1. temperaturewas refluxed for 18 hours
  2. customThe ethanol was evaporated under vacuum
  3. customSeparation of the yellow solid

Sources & evidence

ORD record
ord-e580f35dd67943268ad38c11fa177412
Source dataset
uspto-grants-1997_08
Patent number
US05654436

Reaction notes

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