Water → 7-bromo-N-hydroxybenzo[1,2,5]thiadiazole-4-carbimidoyl chloride

HRID 1505244Notes

Reaction equation

HRID 1505244 reaction equation
[Br:1][C:2]1[C:10]2[C:6](=[N:7][S:8][N:9]=2)[C:5]([CH:11]=[N:12][OH:13])=[CH:4][CH:3]=1.[Cl:14]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:1][C:2]1[C:10]2[C:6](=[N:7][S:8][N:9]=2)[C:5]([C:11]([Cl:14])=[N:12][OH:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 1363510697-Bromo-benzo[1,2,5]thiadiazole-4-carbaldehyde oxime

Product 1

HCID 1363510707-bromo-N-hydroxybenzo[1,2,5]thiadiazole-4-carbimidoyl chlorideYield 83.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-bromo-benzo[1,2,5]thiadiazole-4-carbaldehyde oxime (Example 5.4) (16.65 g) in dimethylformamide (150 ml) was added N-chlorosuccinimide (“NCS”) (10.34 g). The reaction mixture stirred at ambient temperature for 16 hours. Water (750 ml) was added to the reaction mixture and the solids were isolated by filtration to obtain 7-bromo-N-hydroxy-benzo[1,2,5]thiadiazole-4-carbimidoyl chloride (15.77 g) as a yellow solid which was used without further purification.

Workup

  1. customthe solids were isolated by filtration

Sources & evidence

ORD record
ord-94618b5e4b224701b704f0156d49063d
Source dataset
uspto-grants-2015_12
Patent number
US09216973B2

Reaction notes

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