Urea → HCID 69497100, compound

HRID 1814213Notes

Reaction equation

HRID 1814213 reaction equation
[C:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1)#[N:2].[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[NH2:17]C(N)=O>O>[NH:10]=[C:11]1[CH:16]=[CH:15][C:14]([N:17]=[N:7][C:6]2[CH:8]=[CH:9][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)=[CH:13][CH2:12]1

Participants

5

Reactant 3

HCID 1176UreaHCID 6115AnilineHCID 133964-Aminobenzonitrile

Product 1

HCID 69497100HCID 69497100, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8.6 g 4-cyanoaniline were diazotised, analogously to 1.1.2. The reaction mixture was slowly added at 5 to 10° C. to a solution of 6.5 g aniline and 3 g urea in 60 ml water and was stirred at room temperature overnight. The precipitate was filtered off under suction, washed with water and dried. 6.9 g of the orange-coloured 4-imino-4′-cyano-azobenzene were obtained, and were used further without purification. The further synthesis of the monomer was effected analogously to 1.1.1. Monomer 1.1.10 had an f.p. of 174° C., and exhibited a liquid crystalline phase up to 204° C.; λmax=380 nm (DMF). 1.1.11

Workup

  1. filtrationThe precipitate was filtered off under suction
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-c05d4a4691e34215a63c3773069856e9
Source dataset
uspto-grants-2005_04
Patent number
US06875833B2

Reaction notes

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