Hydrochloric Acid → HCID 86630782, compound

HRID 401765Notes

Reaction equation

HRID 401765 reaction equation
Cl.[Cl:2][C:3]1[S:7][C:6]([NH2:8])=[N:5][CH:4]=1.Cl[S:10]([C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([C:23]#[N:24])[CH:14]=1)(=[O:12])=[O:11].Cl>N1C=CC=CC=1>[Cl:2][C:3]1[S:7][C:6]([NH:8][S:10]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([C:23]#[N:24])[CH:14]=2)(=[O:12])=[O:11])=[N:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1487432-Amino-5-chlorothiazole hydrochlorideHCID 86630783Methyl 4-(chlorosulfonyl)-2-cyanobenzoate

Product 1

HCID 86630782HCID 86630782, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-chloro-1,3-thiazol-2-amine hydrochloride (1.15 g, 6.7 mmol, 3 eq) in pyridine (7.5 ml) was added methyl 4-(chlorosulfonyl)-2-cyanobenzoate (Preparation 20, 580 mg, 2.2 mmol, 1 eq) portionwise and the reaction mixture was stirred at room temperature for 1 hour. The mixture was slowly added to 6M HCl (40 ml) and the resulting precipitate was collected by filtration and triturated with MeOH to yield the title compound as a brown solid (138 mg, 0.38 mmol, 17%).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customtriturated with MeOH

Sources & evidence

ORD record
ord-cc06001fce5f453f86bb76735cce3f6e
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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