1,2-Dichloroethane → HCID 1087669, compound

HRID 1666572Notes

Reaction equation

HRID 1666572 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:25][C:26]([C:29]1[S:33][C:32]([NH2:34])=[N:31][N:30]=1)([CH3:28])[CH3:27]>CN(C=O)C.C(OCC)(=O)C.C(Cl)Cl>[CH3:25][C:26]([C:29]1[S:33][C:32]([NH:34][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[I:1])=[N:31][N:30]=1)([CH3:28])[CH3:27]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 69412-Iodobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 170170Buthidazolamine

Product 1

HCID 1087669HCID 1087669, compoundYield 96.8%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Iodobenzoic acid (2 mmol), EDC (2 mmol), and HOBt (4 mmol) were added to 6 ml DCM and stirred at rt for 1 hour. 5-(1,1-dimethylethyl)-1,3,4-thiadiazol-2-amine (2 mmol) was added as a solution in 4 ml DMF. The reaction was stirred at rt for 1 hour and then diluted with ethyl acetate. The solution was washed with 1N HCl, sat. sodium bicarbonate, and brine. The organic layer was dried over sodium sulfate and then evaporated to give N-[5-(1,1-dimethylethyl)-1,3,4-thiadiazol-2-yl]-2-iodobenzamide (750 mg) pure by LCMS.

Workup

  1. stirringThe reaction was stirred at rt for 1 hour
  2. washThe solution was washed with 1N HCl, sat. sodium bicarbonate, and brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-936fa067274146809dc0b5b2115a79af
Source dataset
uspto-grants-2011_10
Patent number
US08044075B2

Reaction notes

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