Diethylenetriamine → UV-328

HRID 1197635Notes

Reaction equation

HRID 1197635 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]=[N:11][C:12]1[CH:17]=[C:16]([C:18]([CH2:21][CH3:22])([CH3:20])[CH3:19])[CH:15]=[C:14]([C:23]([CH2:26][CH3:27])([CH3:25])[CH3:24])[C:13]=1[OH:28])([O-])=O.NCCNCCN>C1(C)C(C)=CC=CC=1>[OH:28][C:13]1[C:14]([C:23]([CH2:26][CH3:27])([CH3:25])[CH3:24])=[CH:15][C:16]([C:18]([CH2:21][CH3:22])([CH3:20])[CH3:19])=[CH:17][C:12]=1[N:11]1[N:10]=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]2=[N:1]1

Participants

4

Reactant 2

HCID 8111Diethylenetriamine2×HCID 1041112-Nitro-2'-hydroxy-3',5'-bis(tert-amyl)azobenzene

Product 1

HCID 33263UV-328Yield 86.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Example 1 is repeated, except that an equivalent amount of 2-nitro-2'-hydroxy-3', 5'-di-tert.-amylazobenzene (91.6% pure) is used instead of 2-nitro-2'-hydroxy-5'-methylazobenzene and a mixture of 60 g of xylene and 40 g of diethylenetriamine is used instead of 80 g of xylene and 20 g of diethylenetriamine. The work up is analogous (filtering off the catalyst, separating off the amine bottom phase, extracting the remaining amine from the xylene top phase with water, concentration and crystallization from xylene/methanol). The title product is isolated in a yield of 86.5% of theory. Melting point: 80°-82° C.

Workup

  1. filtrationThe work up is analogous (filtering off the catalyst
  2. customseparating off the amine bottom phase
  3. extractionextracting the remaining amine from the xylene top phase
  4. concentrationwith water, concentration and crystallization from xylene/methanol)

Sources & evidence

ORD record
ord-bf95436d521849eea75e24f8be9ad931
Source dataset
uspto-grants-1994_01
Patent number
US05276161

Reaction notes

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