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

HRID 536420Notes

Reaction equation

HRID 536420 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 (16.65 g) (Example I4) in N,N-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 resulting solid was isolated by filtration to obtain 7-bromo-N-hydroxybenzo[1,2,5]thiadiazole-4-carbimidoyl chloride (15.77 g) as a yellow solid which was used without further purification.

Workup

  1. customthe resulting solid was isolated by filtration

Sources & evidence

ORD record
ord-4d8fc9ac02904ee08ff639fc6924c068
Source dataset
uspto-grants-2014_10
Patent number
US08859592B2

Reaction notes

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