Water → HCID 19360250, compound

HRID 1728628Notes

Reaction equation

HRID 1728628 reaction equation
[NH2:1][C:2]1[C:3]2[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:4]=2[S:5][CH:6]=1.Cl.[Cl:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.O>CN1CCCC1=O.CO.C(OCC)(=O)C>[ClH:16].[F:13][C:11]([F:14])([F:12])[C:9]1[CH:8]=[CH:7][C:4]2[S:5][CH:6]=[C:2]([NH:1][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[C:3]=2[CH:10]=1

Participants

7

Reactant 3

HCID 962WaterHCID 818524-Chloropyridine hydrochloride2×HCID 193602275-(Trifluoromethyl)benzo[b]thiophen-3-amine2×

Product 1

HCID 19360250HCID 19360250, compoundYield 95.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

A solution of 3-amino-5-trifluoromethylbenzo[b]thiophene (27 g, 124 mmol) and 4-chloropyridine hydrochloride (20.5 g, 137 mmol) in 250 mL of 1-methyl-2-pyrrolidinone was stirred at 70°-80° C. for 1.5 hours. After cooling, the reaction mixture was stirred with water, washed with ether and separated. The aqueous layer was basified with a saturated sodium carbonate solution and the product which precipitated was collected. The reaction was repeated as above with an additional sample of 3-amino-5-trifluoromethylbenzo[b]thiophene (25.6 g, 118 mmol) and 4-chloropyridine hydrochloride (22 g, 148 mmol) in 225 mL of 1-methyl-2-pyrrolidinone. After a similar work-up, the two products were combined and dissolved in 10% methanol in ethyl acetate. The solution was dried (anhydrous magnesium sulfate), filtered and concentrated, yielding a yellow solid. This solid product was washed with ether and filtered to afford 39.1 g of a golden solid. Elution of a portion (3.5 g) of the residue through silica with ethyl acetate via flash column chromatography afforded 3.2 g of a white solid. Conversion of 2.4 g to the hydrochloride salt in 10% methanol in ether afforded 2.6 g of white crystals, mp 318°-319° C.

Workup

  1. temperatureAfter cooling
  2. washwashed with ether
  3. customseparated
  4. customthe product which precipitated
  5. customwas collected
  6. dry with materialThe solution was dried (anhydrous magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customyielding a yellow solid
  10. washThis solid product was washed with ether
  11. filtrationfiltered

Sources & evidence

ORD record
ord-80e61b07abe04c6b98edf71bc3a0c5c7
Source dataset
uspto-grants-1994_07
Patent number
US05328920

Reaction notes

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