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

HRID 1666564Notes

Reaction equation

HRID 1666564 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([NH2:13])=[N:10][N:9]=2)=[CH:4][CH:3]=1.[NH2:14][S:15]([C:18]1[CH:19]=[CH:20][C:21]([Cl:27])=[C:22]([CH:26]=1)[C:23](O)=[O:24])(=[O:17])=[O:16].C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1>C(Cl)Cl>[NH2:14][S:15]([C:18]1[CH:19]=[CH:20][C:21]([Cl:27])=[C:22]([CH:26]=1)[C:23]([NH:13][C:11]1[S:12][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[N:9][N:10]=1)=[O:24])(=[O:17])=[O:16]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 667942-Chloro-5-aminosulfonylbenzoic acidHCID 181649HOAtHCID 5542085-(4-Fluorophenyl)-1,3,4-thiadiazol-2-amine

Product 1

HCID 249594625-(aminosulfonyl)-2-chloro-N-[5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl]benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 20 ml scintillation vial containing a Teflon covered magnetic stir-bar was added commercially available 5-(4-fluorophenyl)-1,3,4-thiadiazol-2-amine (25 mg, 0.128 mmol) and 5-(aminosulfonyl)-2-chlorobenzoic acid (22.3 mg, 0.128 mmol). To this mixture was added EDC (25 mg, 0.128 mmol) and HOAt (18 mg, 0.128 mmol) followed by 3 ml of DCM. The resulting mixture was stirred at room temperature overnight. The product precipitated and was collected by vacuum filtration, washed with 3 ml of MeOH and air-dried under vacuum. Yield of 5-(aminosulfonyl)-2-chloro-N-[5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl]benzamide was (7 mg) as a white powder.

Workup

  1. additionTo a 20 ml scintillation vial containing a Teflon covered magnetic stir-bar
  2. customThe product precipitated
  3. filtrationwas collected by vacuum filtration
  4. washwashed with 3 ml of MeOH
  5. customair-dried under vacuum

Sources & evidence

ORD record
ord-c76c4393bb4e4657af385f3882ed975f
Source dataset
uspto-grants-2011_10
Patent number
US08044075B2

Reaction notes

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