3-Fluorobenzothiohydrazide → Tert-butyl 3-(5-(3-fluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)butylcarbamate

HRID 468050Notes

Reaction equation

HRID 468050 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](=[S:8])[NH:6][NH2:7].[CH3:12][CH:13]([C:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20]>C(O)C.C(Cl)Cl.C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:5]2[S:8][C:24]([CH:13]([CH3:12])[CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[NH:7][N:6]=2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 552816163-FluorobenzothiohydrazideHCID 67214951Tert-butyl 3-methyl-4-oxo-4-phenylbutylcarbamate

Product 1

HCID 67215287Tert-butyl 3-(5-(3-fluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)butylcarbamateYield 48.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 21584144Dichloromethane ethanolSolvent

Procedure

To a solution of 3-fluorobenzothiohydrazide (300 mg, 1.76 mmol) in ethanol/DCM (6 mL/2 mL) was added tert-butyl 3-methyl-4-oxo-4-phenylbutylcarbamate (538 mg, 1.94 mmol). After stirring at room temperature for 16 hours, acetic acid (3 drops) was added and the mixture stirred for another 48 hours. The reaction mixture was then concentrated under reduced pressure and chromatographed (9:1 hexanes/ethyl acetate) to provide the product (366 mg, 48%) as a mixture of diastereomers as a yellow foam.

Workup

  1. stirringthe mixture stirred for another 48 hours
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. customchromatographed (9:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-6b1acd70732649da84552820e4872661
Source dataset
uspto-grants-2014_01
Patent number
US08623895B2

Reaction notes

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