Water → HCID 178424802, compound

HRID 1633262Notes

Reaction equation

HRID 1633262 reaction equation
[N:1]([O-])=O.[Na+].O.[ClH:6].Cl.Cl.[NH2:9][C:10]1[C:15]([NH2:16])=[CH:14][CH:13]=[CH:12][C:11]=1[O:17][CH2:18][CH:19]([OH:33])[CH2:20][NH:21][CH2:22][CH2:23][NH:24][C:25]1[C:30]([CH3:31])=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:32]>C(O)(=O)C>[ClH:6].[ClH:6].[NH:16]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([O:17][CH2:18][CH:19]([OH:33])[CH2:20][NH:21][CH2:22][CH2:23][NH:24][C:25]3[C:30]([CH3:31])=[CH:29][CH:28]=[CH:27][C:26]=3[CH3:32])[C:10]=2[N:9]=[N:1]1

Participants

5

Reactant 3

HCID 962Water2×HCID 20440405HCID 20440405, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 178424802HCID 178424802, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

1.38 g. Sodium nitrite dissolved in 2.2 ml. water are added to a solution, cooled to 0° C., of 9.1 g. 2,3-diamino-1-{2-hydroxy-3-[2-(2,6-dimethylphenylamino)-ethylamino]-propoxy}-benzene trihydrochloride in 12 ml. water and 4.6 ml. glacial acetic acid. After stirring for 2 hours at ambient temperature, the reaction mixture is evaporated to dryness, the residue is taken up in chloroform and the solution is washed with 1M hydrochloric acid and water, dried and evaporated. The residue is recrystallized from ethanol-ethyl acetate, with the addition of active charcoal, to give 2.2 g. (26% of theory) of the desired compound; m.p. 230°-232° C.

Workup

  1. customthe reaction mixture is evaporated to dryness
  2. washthe solution is washed with 1M hydrochloric acid and water
  3. customdried
  4. customevaporated
  5. customThe residue is recrystallized from ethanol-ethyl acetate, with the addition of active charcoal
  6. customto give 2.2 g

Sources & evidence

ORD record
ord-c43345dcb2e3481d9adad062684d0171
Source dataset
uspto-grants-1984_10
Patent number
US04479962

Reaction notes

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