Ammonia → HCID 10857978, compound

HRID 1609376Notes

Reaction equation

HRID 1609376 reaction equation
NC1C([OH:8])=CC(O)=C(N)C=1.[OH-].[Na+].N.[O-]O.C1(C(C)C)C=CC=CC=1.[Cl:25][C:26]1[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[C:28]([N+:35]([O-:37])=[O:36])[C:27]=1[Cl:38]>C(Cl)Cl>[Cl:25][C:26]1[C:27]([Cl:38])=[C:28]([N+:35]([O-:37])=[O:36])[CH:29]=[C:30]([N+:32]([O-:34])=[O:33])[C:31]=1[OH:8]

Participants

7

Reactant 5

HCID 222Ammonia4×HCID 14798Sodium HydroxideHCID 4588214,6-DiaminoresorcinolHCID 110209011,2-Dichloro-3,5-dinitrobenzeneHCID 53627471Cumen hydroperoxide

Product 1

HCID 10857978HCID 10857978, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a preferred embodiment for making diaminoresorcinol, the base, e.g., sodium hydroxide, is first dissolved in refluxing liquid ammonia in an inert atmosphere. The temperature of refluxing liquid ammonia is dependent upon the pressure and is typically between about -50° C. to about -10° C. Under atmospheric pressure conditions, the refluxing temperature of liquid ammonia is about -33° C. A solution of cumene hydroperoxide and 1,2-dichloro-3,5-dinitrobenzene in methylene chloride is then added to the stirred liquid ammonia reaction mixture at a rate such that the temperature remains at the refluxing temperature. Upon completion of the addition, the ammonia is evaporated and 2,3-dichloro-4,6-dinitrophenol may be isolated by pouring the reaction mixture into excess aqueous hydrochloric acid and extracted with ethyl acetate. Preferably, the 2,3-dichloro-4,6-dinitrophenol product is not isolated or purified, but is directly converted to 4,6-diaminoresorcinol, thus making the production of 4,6-diaminoresorcinol from 1,2-dichloro-3,5-dinitrobenzene a "one pot" process.

Workup

  1. customis typically between about -50° C. to about -10° C
  2. customis about -33° C
  3. additionUpon completion of the addition
  4. customthe ammonia is evaporated

Sources & evidence

ORD record
ord-429a71b20f00411088209a83430522f2
Source dataset
uspto-grants-1995_03
Patent number
US05399768

Reaction notes

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