Hydrochloric Acid → HCID 86646187, compound

HRID 1895407Notes

Reaction equation

HRID 1895407 reaction equation
S(Cl)(Cl)=O.[Br:5][C:6]1[CH:7]=[C:8]([C:13](=[O:29])[CH2:14][C:15]([C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=2)(O)[C:16]([F:19])([F:18])[F:17])[CH:9]=[CH:10][C:11]=1[F:12].N1C=CC=CC=1.Cl>C1(C)C=CC=CC=1>[Br:5][C:6]1[CH:7]=[C:8]([C:13](=[O:29])[CH:14]=[C:15]([C:21]2[CH:22]=[C:23]([Cl:28])[CH:24]=[C:25]([Cl:27])[CH:26]=2)[C:16]([F:17])([F:18])[F:19])[CH:9]=[CH:10][C:11]=1[F:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049Pyridine2×HCID 24386Thionyl ChlorideHCID 86673241HCID 86673241, compound

Product 1

HCID 86646187HCID 86646187, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of thionyl chloride (0.618 g, 5.52 mmol) in toluene (1 mL) was added to a mixture of the product from Step A (1.2 g, 2.60 mmol) and pyridine (0.41 g, 5.18 mmol) in toluene (15 mL) at 60-65° C. When the addition was complete, pyridine (0.2 g, 2.53 mmol) was added incrementally to the reaction mixture. When the addition was complete, the mixture was allowed to cool to ambient temperature and then poured into 1N hydrochloric acid (100 mL). The resulting mixture was extracted with ethyl acetate (2×50 mL) and the combined extracts dried and evaporated to give the title product as an oil (1.12 g, 97% yield).

Workup

  1. additionWhen the addition
  2. additionWhen the addition
  3. extractionThe resulting mixture was extracted with ethyl acetate (2×50 mL)
  4. customthe combined extracts dried
  5. customevaporated

Sources & evidence

ORD record
ord-356a818b3f1448d5912d0fbf2f65f087
Source dataset
uspto-grants-2013_08
Patent number
US08513431B2

Reaction notes

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