1,2-Dichloroethane → 5-(aminosulfonyl)-2,3-dichloro-N-[5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl]benzamide

HRID 1666566Notes

Reaction equation

HRID 1666566 reaction equation
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([Cl:15])[C:8]([Cl:14])=[C:9]([CH:13]=1)[C:10]([OH:12])=O)(=[O:4])=[O:3].[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[S:27][C:26]([NH2:28])=[N:25][N:24]=2)=[CH:19][CH:18]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1>C(Cl)Cl>[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([Cl:15])[C:8]([Cl:14])=[C:9]([CH:13]=1)[C:10]([NH:28][C:26]1[S:27][C:23]([C:20]2[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=2)=[N:24][N:25]=1)=[O:12])(=[O:3])=[O:4]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 5542085-(4-Fluorophenyl)-1,3,4-thiadiazol-2-amineHCID 180713352,3-Dichloro-5-sulfamoylbenzoic acid

Product 1

HCID 249594635-(aminosulfonyl)-2,3-dichloro-N-[5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl]benzamideYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 20 ml scintillation vial was added 5-(aminosulfonyl)-2,3-dichlorobenzoic acid (40 mg, 0.148mmol) and commercially available 5-(4-fluorophenyl)-1,3,4-thiadiazol-2-amine (28.9 mg, 0.148 mmol). To this was added EDC (28 mg, 0.148 mmol) and HOAt (20 mg, 0.148 mmol) followed by 3 ml DCM. The reaction mixture was stirred with a Teflon covered magnetic stir-bar at room temperature for overnight. The product was collected by vacuum filtration and air dried, yielding 5-(aminosulfonyl)-2,3-dichloro-N-[5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl]benzamide (31 mg, 47%) as light tan solid.

Workup

  1. filtrationThe product was collected by vacuum filtration and air
  2. customdried

Sources & evidence

ORD record
ord-ca9572fc923b434ab1a7e9882601f1f8
Source dataset
uspto-grants-2011_10
Patent number
US08044075B2

Reaction notes

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