Sodium Bicarbonate → HCID 22147849, compound

HRID 1823875Notes

Reaction equation

HRID 1823875 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([NH:9][NH:10][C:11](=[O:19])[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[N:14][CH:13]=1)=O.ClC1C=CC(C(Cl)=O)=CN=1.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:18][C:15]1[N:14]=[CH:13][C:12]([C:11]2[O:19][C:7]([C:3]3[S:4][CH:5]=[CH:6][C:2]=3[Cl:1])=[N:9][N:10]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27821656-Chloronicotinoyl ChlorideHCID 86587355HCID 86587355, compound

Product 1

HCID 22147849HCID 22147849, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Chloro-nicotinic acid N′-(3-chloro-thiophene-2-carbonyl)-hydrazide: A solution of 3-chloro-thiophene-2-carbonyl hydrazide (70 mg, 0.40 mmol), 6-chloronicotinoyl chloride (76 mg, 0.43 mmol) and dichloromethane (10 mL) was stirred for 5 min. To the solution was added saturated sodium bicarbonate solution (10 mL) and it was stirred for 5 min. The layers were separated and the aqueous phase was extracted with dichloromethane (8×10 mL). Ethyl acetate (50 mL) was added to the combined organic phases, which were dried over anhydrous sodium sulfate, decanted, and concentrated to yield 120 mg (96%) of the title compound as a white powder. 1H NMR (DMSO-d6): 10.89 (s, 1H), 10.37 (s, 1H), 8.89 (d, J=2.19 Hz, 1H), 8.30 (dd, J=8.52, 2.48 Hz, 1H), 7.93 (d, J=5.22 Hz, 1H), 7.72 (d, J=8.25 Hz, 1H), 7.22 (d, J=5.22 Hz, 1H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted with dichloromethane (8×10 mL)
  3. additionEthyl acetate (50 mL) was added to the combined organic phases, which
  4. dry with materialwere dried over anhydrous sodium sulfate
  5. customdecanted
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-99cde192c3854f15a5ce69985c8fdbe3
Source dataset
uspto-grants-2006_05
Patent number
US07041685B2

Reaction notes

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