Chloroacetaldehyde → HCID 58204096, compound

HRID 707823Notes

Reaction equation

HRID 707823 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-c4b1677b90ec46eaa68f165e6d9f90d9
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

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