Diethylenetriamine → Octrizole

HRID 1197633Notes

Reaction equation

HRID 1197633 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][C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:20])[CH3:19])[CH:15]=[CH:14][C:13]=1[OH:26])([O-])=O.NCCNCCN>C1(C)C(C)=CC=CC=1>[OH:26][C:13]1[CH:14]=[CH:15][C:16]([C:18]([CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])([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 1039272-((2-Nitrophenyl)azo)-4-(1,1,3,3-tetramethylbutyl)phenol

Product 1

HCID 62485OctrizoleYield 92%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Example 1 is repeated, except that an equivalent amount of 2-nitro-2'-hydroxy-5'-tert.-octylazobenzene (93% pure) is used instead of 2-nitro-2'-hydroxy-5'-methylazobenzene and a mixture of 60 g of xylene and 40 g of diethylenetriamine instead of 80 g of xylene and 20 g of diethylenetriamine. The hydrogenation is carried out at 45° C. The title product is isolated in a yield of 92% of theory. Melting point: 101°-103° C.

Workup

  1. customis carried out at 45° C

Sources & evidence

ORD record
ord-a50707c22b0945f6848af18c8087e51b
Source dataset
uspto-grants-1994_01
Patent number
US05276161

Reaction notes

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