Chloroacetaldehyde → HCID 12348627, compound

HRID 1506804Notes

Reaction equation

HRID 1506804 reaction equation
Cl[CH2:2][CH:3]=O.[Cl:5][C:6]1[CH:7]=[C:8]([NH:12][C:13]([NH2:15])=[S:14])[CH:9]=[CH:10][CH:11]=1>C(O)C>[Cl:5][C:6]1[CH:7]=[C:8]([NH:12][C:13]2[S:14][CH:2]=[CH:3][N:15]=2)[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 2734794Thiourea, (3-chlorophenyl)- (9CI)

Product 1

HCID 12348627HCID 12348627, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Aqueous chloro acetaldehyde solution (15 mL) was added to a solution of 26A (15.5 g, 80 mmol) in ethanol (150 mL) and stirred at 60° C. for 16 h. The reaction mixture was concentrated in vacuo, and partitioned between ethyl acetate and water. The separated organic layer was washed with saturated NaCl, dried over sodium sulfate and filtered, and the filtrate was concentrated in vacuo. The crude product was purified by flash chromatography using 10% ethyl acetate in hexane to afford the title compound (15 g, 81%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.39 (s, 1H), 7.96 (t, J=2.1 Hz, 1H), 7.45-7.38 (dd, J1=2.0 Hz, J2=8.4 Hz, 1H), 7.37-7.26 (m, 2H), 7.02-6.95 (m, 2H). ESI-MS m/z: 211 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompartitioned between ethyl acetate and water
  3. washThe separated organic layer was washed with saturated NaCl
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-fb2e156f93d44c2ebfedcc268917fbeb
Source dataset
uspto-grants-2015_12
Patent number
US09221766B2

Reaction notes

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