Sodium Nitrite → 4-(3-bromo-5-chlorophenoxy)-5-chloro-1H-1,2,3-benzotriazole

HRID 505522Notes

Reaction equation

HRID 505522 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[O:5][C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]([NH2:13])[C:7]=1[NH2:14].[N:19]([O-])=O.[Na+]>C(O)(=O)C.O.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[O:5][C:6]1[C:7]2[N:14]=[N:19][NH:13][C:8]=2[CH:9]=[CH:10][C:11]=1[Cl:12]

Participants

6

Reactant 2

HCID 23668193Sodium NitriteHCID 568337453-(3-Bromo-5-chlorophenoxy)-4-chlorobenzene-1,2-diamine

Product 1

HCID 1784778354-(3-bromo-5-chlorophenoxy)-5-chloro-1H-1,2,3-benzotriazole

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(3-bromo-5-chlorophenoxy)-4-chlorobenzene-1,2-diamine (4.97 g, 14.3 mmol) in acetic acid (25 mL) was cooled to 15° C. under N2 and sodium nitrite (1.08 g, 15.7 mmol) in water (39.3 mL) was added dropwise. After 1.5 hours, the reaction was diluted with EtOAc (300 mL), and the organic phase was separated and washed with water (3×100 mL). The organic phase was then dried (MgSO4), filtered, concentrated to afford the title product. LRMS (M+1) 359.7.

Workup

  1. customthe organic phase was separated
  2. washwashed with water (3×100 mL)
  3. dry with materialThe organic phase was then dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-74226e5518c74d158f96955cd801b2e6
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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