Water → n-Hydroxy-2-(4-isopropoxyphenoxy)-1,3-thiazole-5-carboximidoyl chloride

HRID 404866Notes

Reaction equation

HRID 404866 reaction equation
[CH:1]([O:4][C:5]1[CH:19]=[CH:18][C:8]([O:9][C:10]2[S:11][C:12]([CH:15]=[N:16][OH:17])=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[Cl:20]N1C(=O)CCC1=O.O>CN(C)C=O>[OH:17][N:16]=[C:15]([Cl:20])[C:12]1[S:11][C:10]([O:9][C:8]2[CH:18]=[CH:19][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[CH:6][CH:7]=2)=[N:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 861014162-(4-Isopropoxyphenoxy)-1,3-thiazole-5-carbaldehyde oxime

Product 1

HCID 131731603n-Hydroxy-2-(4-isopropoxyphenoxy)-1,3-thiazole-5-carboximidoyl chlorideYield 96.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 1D (7.77 g, 0.028 mol) in N,N-dimethylformamide was added N-chlorosuccinimide (4.0 g, 0.029 mol) and the solution was stirred at room temperature for 6 hours. Water was added and the reaction mixture stirred for 30 minutes. The precipitate was filtered and air-dried to give 8.45 g of product as an off-white solid (96% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.28 (d, J=5.88 Hz, 6H) 4.53-4.70 (m, 1 H) 6.95-7.07 (m, 2H) 7.26-7.37 (m, 2H) 7.67 (s, 1H) 12.41 (s, 1H). MS (ESI) m/z 294.0 (M−18)+.

Workup

  1. stirringthe reaction mixture stirred for 30 minutes
  2. filtrationThe precipitate was filtered
  3. customair-dried

Sources & evidence

ORD record
ord-d2f43e63cf9b44f784b43f9060fa01fe
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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