Water → 2-chloro-4-methoxyphenoxy-N-hydroxy-1,3-thiazole-5-carboximidoyl chloride

HRID 404899Notes

Reaction equation

HRID 404899 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:3]=1[O:4][C:5]1[S:6][C:7]([CH:10]=[N:11][OH:12])=[CH:8][N:9]=1.[Cl:19]N1C(=O)CCC1=O.O>CN(C)C=O>[Cl:1][C:2]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:3]=1[O:4][C:5]1[S:6][C:7]([C:10]([Cl:19])=[N:11][OH:12])=[CH:8][N:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 1317316062-Chloro-4-methoxyphenoxy-1,3-thiazole-5-carbaldehyde oxime

Product 1

HCID 1317316072-chloro-4-methoxyphenoxy-N-hydroxy-1,3-thiazole-5-carboximidoyl chlorideYield 95.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 30C (12 g, 42 mmol) in N,N-dimethyl formamide (80 mL) was added N-chlorosuccinimide (5.6 g, 42 mmol). The mixture was stirred at ambient temperature for 16 hours, water (1000 mL) was added and the resulting suspension was filtered. The solids were dried in a vacuum oven to provide 12.8 g of the title compound (95%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.82 (s, 3H) 7.04 (dd, J=8.82, 2.94 Hz, 1H) 7.26 (d, J=2.94 Hz, 1H) 7.54 (d, J=9.19 Hz, 1H) 7.66 (s, 1H) 12.48 (s, 1H); MS (ESI) m/z 319.9 (M+H)+.

Workup

  1. filtrationthe resulting suspension was filtered
  2. customThe solids were dried in a vacuum oven

Sources & evidence

ORD record
ord-953c1d7e82f940a19090e4b2429a43ff
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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