2,5-Dichlorobenzoic acid → 2,5-dichloro-N-(4-chloro-2-methyl-benzothiazol-5-yl)-benzamide

HRID 1766326Notes

Reaction equation

HRID 1766326 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.[Cl:12][C:13]1[C:18]2[N:19]=[C:20]([CH3:22])[S:21][C:17]=2[CH:16]=[CH:15][C:14]=1[NH2:23].C(N(CC)CC)C>S(Cl)(Cl)=O.C1COCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([NH:23][C:14]1[CH:15]=[CH:16][C:17]2[S:21][C:20]([CH3:22])=[N:19][C:18]=2[C:13]=1[Cl:12])=[O:6]

Participants

6

Reactant 3

HCID 57842,5-Dichlorobenzoic acidHCID 8471TriethylamineHCID 112178574-Chloro-2-methylbenzo[d]thiazol-5-amine

Product 1

HCID 211102722,5-dichloro-N-(4-chloro-2-methyl-benzothiazol-5-yl)-benzamideYield 52%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 24386Thionyl ChlorideSolvent

Procedure

Reaction of 2,5-dichlorobenzoic acid (145 mg, 0.76 mmol) in thionyl chloride (5 mL) then with 4-chloro-2-methyl-benzothiazol-5-ylamine (50 mg, 0.25 mmol) in presence of triethylamine (0.5 mL) in THF (2 mL) according to method B gave 2,5-dichloro-N-(4-chloro-2-methyl-benzothiazol-5-yl)-benzamide (50 mg, 0.13 mmol, 52% yield) as a white powder after purification by chromatography on silica gel(eluent: DCM).

Sources & evidence

ORD record
ord-2808113753c240eb9c55d2c9d55b5975
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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