Sodium Azide → Methyl 6-azido-4-(4-bromo-2-chlorophenylamino)-5-chloronicotinate

HRID 1161804Notes

Reaction equation

HRID 1161804 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][N:12]=[C:11](Cl)[C:10]=2[Cl:20])=[C:4]([Cl:21])[CH:3]=1.[N-:22]=[N+:23]=[N-:24].[Na+]>CN(C=O)C.O>[N:22]([C:11]1[C:10]([Cl:20])=[C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[Cl:21])[C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][N:12]=1)=[N+:23]=[N-:24]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 11603943Methyl 4-(4-bromo-2-chlorophenylamino)-5,6-dichloronicotinate

Product 1

HCID 59519382Methyl 6-azido-4-(4-bromo-2-chlorophenylamino)-5-chloronicotinateYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl 4-(4-bromo-2-chlorophenylamino)-5,6-dichloronicotinate (1.690 g, 4.14 mmol) was suspended in 30 ml DMF and the suspension was heated until everything went into solution. It was cooled down to room temperature and to that solution was added solid sodium azide (0.533 g, 8.2 mmol). The yellow solution was stirred for 17 h at room temperature and was diluted with water. The precipitate was filtered, washed with water and hexanes and dried in oil-pump vacuo at 50° C. for 2 h to obtain the title compound as a light-brown solid (1.5422 g, 90%). 1H-NMR (300 MHz, DMSO-D6): δ=9.85 (s, 1H), 8.90 (s, 1H), 7.80-7.79 (d, 1H), 7.46-7.40 (dd, 1H), 6.95-6.90 (d, 1H), 3.80 (s, 3H).

Workup

  1. temperaturethe suspension was heated until everything
  2. filtrationThe precipitate was filtered
  3. washwashed with water and hexanes
  4. customdried in oil-pump vacuo at 50° C. for 2 h

Sources & evidence

ORD record
ord-200bcc3bee6b4f88bcda658c05afdb2b
Source dataset
uspto-grants-2010_10
Patent number
US07820664B2

Reaction notes

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