Thionyl Chloride → HCID 59652740, compound

HRID 1662838Notes

Reaction equation

HRID 1662838 reaction equation
NC1C=CC([Cl:11])=C(C=1)C(O)=O.Cl.C(Cl)(=O)C1C=CC=NC=1.[Cl:22][C:23]1[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:40])[C:34]2[CH:39]=[CH:38][CH:37]=[N:36][CH:35]=2)=[CH:28][C:24]=1[C:25](O)=[O:26].S(Cl)(Cl)=O>C1COCC1.ClCCl>[Cl:22][C:23]1[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:40])[C:34]2[CH:39]=[CH:38][CH:37]=[N:36][CH:35]=2)=[CH:28][C:24]=1[C:25]([Cl:11])=[O:26]

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 378795-Amino-2-chlorobenzoic acidHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 23825770HCID 23825770, compound

Product 1

HCID 59652740HCID 59652740, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-amino-2-chlorobenzoic acid (1.71 g, 10 mmol) and TEA (6.96 mL, 50 mmol) in THF (50 mL) was added nicotinoyl chloride hydrochloride (1.78 g, 10 mmol) solid portion-wise. After 1 h stirring at room temperature, product was isolated through filtration as a white solid. The solid was washed with water and dried (1.85 g, 67%). The solid, 2-chloro-5-(nicotinamido)benzoic acid (1.0 g, 3.62 mmol) was suspended in dichloromethane (50 mL) and treated with thionyl chloride (1.57 mL, 36.2 mmol) at reflux for 6 hr. The reaction mixture was evaporated, and the residue was dissolved in hexane-ethyl acetate mixture (100 mL, 6:4) and quickly filtered through a short silica plug. On evaporation of solvent, the title compound was obtained as a white solid (873 mg, 82%).

Workup

  1. customproduct was isolated through filtration as a white solid
  2. washThe solid was washed with water
  3. customdried (1.85 g, 67%)
  4. temperatureat reflux for 6 hr
  5. customThe reaction mixture was evaporated
  6. dissolutionthe residue was dissolved in hexane-ethyl acetate mixture (100 mL, 6:4)
  7. filtrationquickly filtered through a short silica plug
  8. customOn evaporation of solvent

Sources & evidence

ORD record
ord-5ac6f544cd0542ab94608c19a65c5beb
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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