Chloroacetaldehyde → HCID 66894752, compound

HRID 252842Notes

Reaction equation

HRID 252842 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](=[S:8])[NH2:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].Cl[CH2:15][CH:16]=O>C(O)C>[N+:11]([C:3]1[CH:4]=[C:5]([C:6]2[S:8][CH:15]=[CH:16][N:7]=2)[CH:9]=[CH:10][C:2]=1[NH2:1])([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 59736881HCID 59736881, compound

Product 1

HCID 66894752HCID 66894752, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred suspension of 220 (500 mg, 2.53 mmol) in ethanol (15 mL) was added chloroacetaldehyde (50% solution in water, 0.796 ml, 5.0 mmol). The mixture was heated at 80° C. for 18 hours, evaporated under reduced pressure and the residue was dissolved in DCM, washed with brine, dried with sodium sulfate and concentrated. The crude material was purified by flash chromatography on silica gel, eluents hexane-EtOAc (4:1), then EtOAC (100%), to afford the title compound 221a (104 mg, 19% yield). 1H NMR: (CD3OD) δ (ppm): 8.62 (d, J=2.0 Hz, 1H), 7.91 (dd, J=2.4, 8.8 Hz, 1H), 7.78 (d, J=3.2 Hz, 1H), 7.51 (d, J=3.2 Hz, 1H), 7.07 (d, J=8.8 Hz, 1H). MS: (calc.) 221.2; (obt.) 222.1 (MH)+.

Workup

  1. customevaporated under reduced pressure
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with brine
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated
  6. customThe crude material was purified by flash chromatography on silica gel, eluents hexane-EtOAc (4:1)

Sources & evidence

ORD record
ord-fb091e2f28e34210942fec90f75a5ade
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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