Butanal → HCID 72474427, compound

HRID 2075300Notes

Reaction equation

HRID 2075300 reaction equation
COCCOCCOC.[CH2:10]([N:13]1[C:17](=[O:18])[CH2:16][NH:15][C:14]1=[S:19])[CH:11]=[CH2:12].N1CCOCC1.[CH:26](=O)[CH2:27][CH2:28][CH3:29]>C(OCC)(=O)C>[CH2:10]([N:13]1[C:17](=[O:18])[C:16](=[CH:26][CH2:27][CH2:28][CH3:29])[NH:15][C:14]1=[S:19])[CH:11]=[CH2:12]

Participants

6

Reactant 4

HCID 261ButanalHCID 8083MorpholineHCID 8150DiglymeHCID 3032418Hydantoin, 3-allyl-2-thioxo-

Product 1

HCID 72474427HCID 72474427, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A flask equipped with a reflux condenser, magnetic stirrer, and nitrogen atmosphere was charged with diglyme (10 mL), 3-allylthiohydantoin (1.0 g, 0.0064 mol), morpholine (0.56 g, 0.0064 mol), and freshly distilled butyraldehyde (0.94 g, 0.13 mol). The mixture was heated in a 70° oil bath for 250 min and, after cooling, was diluted with 20 mL of ethyl acetate. The resulting solution was washed with 2×10 mL 1.2 M HCl, 10 mL of water, and 10 mL of saturated aqueous NaCl. The solution was then filtered through 1 PS paper and concentrated to dryness at aspirator pressure and then high vacuum. The light orange crystalline residue weighed 1.26 g (97%). An HPLC trace at 215 nm indicated that the major product comprised 92% of the mixture. Another component (5%), with a nearly identical ultraviolet spectrum, eluted slightly more slowly. This possibly represents the other geometric isomer. NMR (CDCl3) δ 10 (bs, 1H), 5.2-6.3 (m, 4H), 4.6 (d, 2H), 2.3 (quart., 2H), 1.8 (sex., 2H), 1.0 (t, 3H).

Workup

  1. customA flask equipped with a reflux condenser, magnetic stirrer
  2. temperatureThe mixture was heated in a 70° oil bath for 250 min
  3. temperatureafter cooling
  4. washThe resulting solution was washed with 2×10 mL 1.2 M HCl, 10 mL of water, and 10 mL of saturated aqueous NaCl
  5. filtrationThe solution was then filtered through 1 PS paper
  6. concentrationconcentrated to dryness at aspirator pressure
  7. washAnother component (5%), with a nearly identical ultraviolet spectrum, eluted slightly more slowly

Sources & evidence

ORD record
ord-e420d0a3325d41ec82426728167d4c6c
Source dataset
uspto-grants-2011_04
Patent number
US07919630B2

Reaction notes

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