Acetaldehyde → HCID 10220835, compound

HRID 2287330Notes

Reaction equation

HRID 2287330 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:13][CH3:14])[C:5]([NH2:12])=[C:6]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:7]=1.[CH:15](=O)[CH3:16].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:13][CH3:14])[C:5]2[NH:12][CH:15]([CH3:16])[NH:11][S:8](=[O:10])(=[O:9])[C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 9942759HCID 9942759, compound

Product 1

HCID 10220835HCID 10220835, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a 25 mL RB flask was added 5-chloro-3-ethyl-2-aminobenzenesulfonamide D (0.4074 g, 1.74 mmol), 8.5 mL acetonitrile, and 3Å molecular sieves. The stirring solution was cooled to 0° C. and acetaldehyde (0.15 mL, 2.68 mmol) and (±) 10-camphor sulphonic acid (catalytic) were added. After 1 h at 0° C., the reaction was filtered through Celite and solvent was removed to give crude D1. The light brown solid was dissolved in EtOAc, passed through silica, and concentrated to give pure D1 (0.4426 g, 98%), m.p. 181-183° C. 1H NMR (300 MHz, DMSO): δ7.70 (1H, d, J=11.8 Hz), 7.35 (1H, d, J=2.2 Hz), 7.21 (1H, d, J=2.2 Hz), 6.24 (1H, s), 4.80 (1H, m), 2.52 (2H, m), 1.48 (3H, d, 7.1 Hz), 1.13 (3H, t, J=7.4 Hz). 13C NMR (500 MHz, DMS0): δ140.2, 132.4, 131.1, 122.2, 120.5, 120.0, 62.2, 23.2, 20.1, 12.7. FT-IR (KBr): 3405.9, 3232.5, 3001.5, 2942.7, 2884.0, 1490.5, 1438.5, 1309.6, 1282.4, 1160.2, 1140.1, 864,5, 743.8, 718.0, 567.5 cm-1. HRMS: M+ calculated=260.0386, found=260.0386.

Workup

  1. filtrationthe reaction was filtered through Celite and solvent
  2. customwas removed

Sources & evidence

ORD record
ord-1f8e1629692b48dfa7f42afa38aa2cae
Source dataset
uspto-grants-2000_07
Patent number
US06083947

Reaction notes

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