Isopropanol → HCID 118033097, compound

HRID 590517Notes

Reaction equation

HRID 590517 reaction equation
[C:1]([S:4][CH2:5]/[CH:6]=[C:7]1\[CH2:8][C:9]([CH3:24])([CH3:23])[CH2:10][C:11]2[S:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Br:22])[CH:17]=3)=[CH:14][C:15]\1=2)(=[NH:3])[NH2:2].C(O)(C)C.[OH-].[Na+]>Cl>[Br:22][C:18]1[CH:17]=[C:16]([C:13]2[S:12][C:11]3[CH2:10][C:9]([CH3:24])([CH3:23])[CH2:8][C:7]4([CH2:6][CH2:5][S:4][C:1]([NH2:2])=[N:3]4)[C:15]=3[CH:14]=2)[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 3776Isopropanol2×HCID 14798Sodium HydroxideHCID 90070481HCID 90070481, compound

Product 1

HCID 118033097HCID 118033097, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

(E)-2-(2-(3-Bromophenyl)-6,6-dimethyl-6,7-dihydrobenzo[b]thiophen-4(5H)-ylidene)ethyl carbamimidothioate (0.31 g, 0.65 mmol) was suspended in conc. HCl (aq.) (10 mL) and iso-propanol (10 mL) and refluxed for 2 h. Further portions of iso-propanol (5 mL) and conc. HCl (aq.) (15 mL) were added and the mixture was refluxed a further 18 hr. The mixture was cooled in an ice bath and then neutralised with aqueous 2 M NaOH solution. The aqueous layer was then extracted with dichloromethane (×3). The organic phases were combined, dried (MgSO4) and concentrated in vacuo to afford the title compound (0.131 g, 48%).

Workup

  1. temperaturethe mixture was refluxed a further 18 hr
  2. temperatureThe mixture was cooled in an ice bath
  3. extractionThe aqueous layer was then extracted with dichloromethane (×3)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-689e83ee6ee44e1f8fd65ae2a9b4786b
Source dataset
uspto-grants-2016_01
Patent number
US09233982B2

Reaction notes

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