Sodium Carbonate → HCID 57551211, compound

HRID 1644649Notes

Reaction equation

HRID 1644649 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([NH:12][NH2:13])=O)=[CH:5][CH:4]=1.[N:16]([C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:28][C:29]2[S:30][CH:31]=[CH:32][N:33]=2)(=[O:27])=[O:26])=[CH:21][CH:20]=1)=[C:17]=[S:18].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[S:30]1[CH:31]=[CH:32][N:33]=[C:29]1[NH:28][S:25]([C:22]1[CH:21]=[CH:20][C:19]([NH:16][C:17]2[S:18][C:10]([CH2:9][C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:15])([F:14])[F:1])=[CH:4][CH:5]=3)=[N:12][N:13]=2)=[CH:24][CH:23]=1)(=[O:26])=[O:27]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 44674964-Isothiocyanato-N-2-thiazolylbenzenesulfonamideHCID 43237029HCID 43237029, compound

Product 1

HCID 57551211HCID 57551211, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of (4-trifluoromethyl-phenyl)-acetic acid hydrazide (55 mg, 0.25 mmol, 1.5 equiv), 4-isothiocyanato-N-thiazol-2-yl-benzenesulfonamide (50 mg, 0.2 mmol, 1.0 equiv) and sodium carbonate (20 mg, 0.18 mmol, 1.1 equiv) in 1.0 mL of ethanol was heated at 85° C. After 16 h, the heterogeneous reaction mixture was concentrated in vacuo, diluted with 500 μL of acetonitrile, filtered, and purified via reverse phase HPLC. The fraction containing product was lyophilized to afford the product as an off-white solid (15 mg, 20%).

Workup

  1. concentrationthe heterogeneous reaction mixture was concentrated in vacuo
  2. additiondiluted with 500 μL of acetonitrile
  3. filtrationfiltered
  4. custompurified via reverse phase HPLC
  5. additionThe fraction containing product

Sources & evidence

ORD record
ord-2fdb93d8572e4a72b3617c5d02932de3
Source dataset
uspto-grants-2012_02
Patent number
US08124610B2

Reaction notes

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