Triethylamine → HCID 46938503, compound

HRID 874722Notes

Reaction equation

HRID 874722 reaction equation
[C:1]1([CH3:25])[CH:6]=[CH:5][C:4]([S:7]([CH:10]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([Br:24])[CH:15]=2)[NH:11][CH:12]=O)(=[O:9])=[O:8])=[CH:3][CH:2]=1.O=P(Cl)(Cl)Cl.CCN(CC)CC>COCCOC>[Br:24][C:16]1[CH:15]=[C:14]([CH:10]([N+:11]#[C-:12])[S:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:25])=[CH:6][CH:5]=2)(=[O:9])=[O:8])[CH:19]=[C:18]([O:20][CH3:21])[C:17]=1[O:22][CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 46938395HCID 46938395, compound

Product 1

HCID 46938503HCID 46938503, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

Compound 3b (4.75 g, 10.75 mmol) was suspended in dry DME (100 mL) and cooled to −10° C. POCl3 (3.1 mL, 33.1 mol) was added and a mixture of Et3N (7.5 mL, 53.8 mmol) in DME (10 mL) was dropped slowly to the reaction mixture. After stirring for 2 h at −5° C., the reaction mixture was poured into ice water. The water phase was extracted with ethyl acetate, the organic phase was washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, filtered and concentrated in vacuum. By refrigeration over night a brown solid crystallized from the residue, which was collected and dried in vacuum. Yield: 2.75 g (6.71 mmol, 62%); brown solid of mp 109-110° C.; νmax (ATR)/cm−1 2915, 2135, 1593, 1569, 1489, 1452, 1420, 1325, 1295, 1275, 1238, 1199, 1136, 1081, 1048, 1003, 862, 826, 759, 705, 670; 1H NMR (300 MHz, CDCl3) δ 2.47 (3H, s), 3.81 (3H, s), 3.86 (3H, s), 5.46 (1H, s), 6.81 (1H, d, J=2.2 Hz), 7.01 (1H, d, J=2.2 Hz), 7.35 (2H, d, J=8.3 Hz), 7.64 (2H, d, J=8.3 Hz); 13C NMR (75.5 MHz, CDCl3) δ 321.8, 56.2, 60.7, 75.5, 111.5, 117.8, 123.2, 125.0, 129.9, 130.0, 130.5, 146.9, 148.5, 153.6, 166.6; m/z (EI) 256 (52), 254 (45), 244 (78), 242 (100), 200 (30), 123 (48), 91 (31).

Workup

  1. additionwas dropped slowly to the reaction mixture
  2. extractionThe water phase was extracted with ethyl acetate
  3. washthe organic phase was washed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customBy refrigeration over night a brown solid crystallized from the residue, which
  8. customwas collected
  9. customdried in vacuum

Sources & evidence

ORD record
ord-4d9812fd222c40a28c18f45c0b528ed9
Source dataset
uspto-grants-2015_03
Patent number
US08980933B2

Reaction notes

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