Dithionite → N-(beta-ureidoethyl) para-phenylenediamine

HRID 436331Notes

Reaction equation

HRID 436331 reaction equation
[NH:1]([CH2:5][CH2:6][NH:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)[C:2]([NH2:4])=[O:3].[OH-].[Na+].S(S([O-])=O)([O-])=O>>[NH:1]([CH2:5][CH2:6][NH:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)[C:2]([NH2:4])=[O:3]

Participants

4

Reactant 3

HCID 1086DithioniteHCID 14798Sodium HydroxideHCID 73423441-(2-Ureidoethylamino)-4-nitrobenzene

Product 1

HCID 53869830N-(beta-ureidoethyl) para-phenylenediamine

Conditions

Temperature
60 °C

Procedure

94 g (0.42 mole) of para-[N-(β-ureidoethyl)]amino nitrobenzene is added little by little, while stirring, to 950 cm3 of a 3 N solution of NaOH containing 285 g of technical hydrosulfite, which has first been heated to 60° C. When the addition has been completed the reaction mixture is kept at 70° C until decoloration is complete. The mixture is then filtered, cooled and dried after salting out. The result is 46 g of N-(β-ureidoethyl) para-phenylenediamine which, after recrystallization in isopropyl alcohol, melts at 126°.

Workup

  1. additionWhen the addition
  2. customis kept at 70° C until decoloration
  3. filtrationThe mixture is then filtered
  4. temperaturecooled
  5. customdried
  6. customafter recrystallization in isopropyl alcohol

Sources & evidence

ORD record
ord-f3cd4e549376429785f051fc6aa95231
Source dataset
uspto-grants-1977_02
Patent number
US04008272

Reaction notes

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