Hydrochloric Acid → HCID 178486932, compound

HRID 57278Notes

Reaction equation

HRID 57278 reaction equation
[F:1][C:2]1[C:3](OC)=[CH:4][C:5]2[S:9][C:8]([C:10](=[C:13]([C:15]3O[CH:17]=[CH:18][CH:19]=3)O)[C:11]#[N:12])=N[C:6]=2[CH:20]=1.[C:23]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClC(C1OC=CC=1)=C(C1SC2C=C(OC)C(F)=CC=2N=1)C#N.[OH2:64].[NH2:65][NH2:66].Cl.[OH-:68].[NH4+:69]>ClCCl.C(Cl)(Cl)(Cl)Cl.CO>[F:1][C:2]1[C:20]([O:68][CH3:23])=[CH:6][C:5]2[S:9][C:8]([C:10]3[C:13]([C:15]4[O:64][CH:17]=[CH:18][CH:19]=4)=[N:66][NH:65][C:11]=3[NH2:12])=[N:69][C:4]=2[CH:3]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 14923Ammonium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 86608763HCID 86608763, compoundHCID 1363358052-(5-Fluoro-6-methoxybenzothiazol-2-yl)-3-furan-2-yl-3-hydroxyacrylonitrile

Product 1

HCID 178486932HCID 178486932, compoundYield 21%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-(5-fluoro-6-methoxybenzothiazol-2-yl)-3-furan-2-yl-3-hydroxyacrylonitrile (70 mg, 0.199 mmol) in anhydrous dichloromethane (3 mL) and carbon tetrachloride (2 mL) was added triphenylphosphine (175 mg, 0.667 mmol). The reaction mixture was stirred at reflux for three hours then at room temperature overnight to give a dark brown solution containing 3-chloro-2-(5-fluoro-6-methoxybenzothiazol-2-yl)-3-furan-2-ylacrylonitrile. Hydrazine monohydrate (30 μL, 0.62 mmol) and methanol (1 mL) were then added and the solution was refluxed for 2 hrs. At this point, conc. HCl (0.7 mL) was added and the solution was refluxed for an additional hour. The mixture was then cooled to room temperature and neutralized with ammonium hydroxide. The solvent was evaporated and the crude product was purified by flash column chromatography eluting with CH2Cl2:MeOH=9:1 to yield 15 mg (21%) of the title compound as a brown solid. MS (m/z, ES+): 331.1 (M+1, 100%).

Workup

  1. temperatureat reflux for three hours
  2. customat room temperature overnight to give a dark brown solution
  3. temperaturethe solution was refluxed for 2 hrs
  4. temperaturethe solution was refluxed for an additional hour
  5. customThe solvent was evaporated
  6. customthe crude product was purified by flash column chromatography
  7. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-da628d9aa9e949c7b1f52777471105a7
Source dataset
uspto-grants-2016_09
Patent number
US09434720B2

Reaction notes

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