Chloroacetaldehyde → HCID 58204096, compound

HRID 1190282Notes

Reaction equation

HRID 1190282 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6]3[N:7]=[C:8]([C:14]([NH:16][CH:17]([CH3:19])[CH3:18])=[NH:15])[S:9][C:10]=3[CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1.Cl[CH2:23][CH:24]=O.C(=O)(O)[O-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6]3[N:7]=[C:8]([C:14]4[N:16]([CH:17]([CH3:19])[CH3:18])[CH:23]=[CH:24][N:15]=4)[S:9][C:10]=3[CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 516892Sodium BicarbonateHCID 178457530HCID 178457530, compound

Product 1

HCID 58204096HCID 58204096, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 8-bromo-N-isopropyl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxamidine (878 mg, 2.4 mmol) in THF (15 mL) was added chloroacetaldehyde solution (˜50 wt. % in H2O, 7.53 mL, 47.9 mmol) and aqueous saturated sodium bicarbonate solution (6 mL) at RT. The mixture was heated to 80° C. with rapid stirring. After heating for 20 hours the mixture was allowed to cool to RT and was extracted with DCM (150 mL). The organic layer was washed with water followed by brine, dried (Na2SO4) and concentrated in vacuo. The resultant residue was purified by flash chromatography (SiO2, gradient 0-100% EtOAc in cyclohexane) to afford the title compound (900 mg, 96%). LCMS RT=4.90 min, [M+H]+=390/392

Workup

  1. temperatureAfter heating for 20 hours the mixture
  2. temperatureto cool to RT
  3. extractionwas extracted with DCM (150 mL)
  4. washThe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified by flash chromatography (SiO2, gradient 0-100% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-81b2aba11c7341a292b373e342f36eae
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

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