Hydrochloric Acid → HCID 57732040, compound

HRID 401777Notes

Reaction equation

HRID 401777 reaction equation
Cl.[NH2:2][C:3]1[S:4][C:5]([Cl:8])=[CH:6][N:7]=1.Cl[S:10]([C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([Cl:23])[CH:14]=1)(=[O:12])=[O:11].Cl>N1C=CC=CC=1>[Cl:23][C:15]1[CH:14]=[C:13]([S:10]([NH:2][C:3]2[S:4][C:5]([Cl:8])=[CH:6][N:7]=2)(=[O:12])=[O:11])[CH:22]=[CH:21][C:16]=1[C:17]([O:19][CH3:20])=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1487432-Amino-5-chlorothiazole hydrochlorideHCID 186290272-chloro-4-(chlorosulfonyl)benzoic acid methyl ester

Product 1

HCID 57732040HCID 57732040, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-amino-5-chlorothiazole hydrochloride (2.62 g, 15.3 mmol, 3 eq) in pyridine (10 ml) was added methyl 4-(chlorosulfonyl)-2-chlorobenzoate (2.28 g, 5.1 mmol, 1 eq) portionwise and the reaction mixture stirred at room temperature for 1 hour. The solution was added to 6M HCl (40 ml) and the resultant precipitate collected by filtration. The crude material was triturated with t-butylmethyl ether to yield the title compound (410 mg, 1.1 mmol, 22%).

Workup

  1. filtrationthe resultant precipitate collected by filtration
  2. customThe crude material was triturated with t-butylmethyl ether

Sources & evidence

ORD record
ord-54cdbce37fe54f38a10572c6bf7cdff5
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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