Benzenediazonium, 4-chloro-2-nitro-, chloride → 5-Chloro-2-nitro-2'-hydroxy-3',5'-di-(4-chloro-alpha-cumyl)azobenzene

HRID 1281065Notes

Reaction equation

HRID 1281065 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([C:9]2[CH:14]=[C:13]([C:15]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)([CH3:17])[CH3:16])[CH:12]=[CH:11][C:10]=2[OH:25])([CH3:8])[CH3:7])=[CH:4][CH:3]=1.[Cl-:28].Cl[C:30]1[CH:35]=[CH:34][C:33]([N+:36]#[N:37])=[C:32]([N+:38]([O-:40])=[O:39])[CH:31]=1>>[Cl:28][C:35]1[CH:30]=[CH:31][C:32]([N+:38]([O-:40])=[O:39])=[C:33]([N:36]=[N:37][C:11]2[CH:12]=[C:13]([C:15]([C:18]3[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=3)([CH3:16])[CH3:17])[CH:14]=[C:9]([C:6]([C:5]3[CH:26]=[CH:27][C:2]([Cl:1])=[CH:3][CH:4]=3)([CH3:8])[CH3:7])[C:10]=2[OH:25])[CH:34]=1

Participants

3

Reactant 2

HCID 10420991Benzenediazonium, 4-chloro-2-nitro-, chlorideHCID 226643982,4-Di-(4-chloro-alpha-cumyl)phenol

Product 1

HCID 1356741165-Chloro-2-nitro-2'-hydroxy-3',5'-di-(4-chloro-alpha-cumyl)azobenzene

Procedure

The title compound is prepared according to the procedure of Example 23 using 45 g of 2,4-di-(4-chloro-α-cumyl)phenol prepared in Example 6 and 138 g of the diazonium salt solution prepared in Example 11 in a yield of 66.3 g. The desired product is a crimson red solid containing some residual salt and melts at 163-165° C. The structure is confirmed by 1Hnmr and mass spectroscopy analyses.

Workup

  1. customThe title compound is prepared
  2. additioncontaining some residual salt and melts at 163-165° C

Sources & evidence

ORD record
ord-ee22d880c30944b68e07dbb9f0feb2c4
Source dataset
uspto-grants-2002_09
Patent number
US06451887B1

Reaction notes

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