Triethylamine → HCID 46938504, compound

HRID 874723Notes

Reaction equation

HRID 874723 reaction equation
[C:1]1([CH3:27])[CH:6]=[CH:5][C:4]([S:7]([CH:10]([C:14]2[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[C:17]([O:23][CH3:24])=[C:16]([O:25][CH3:26])[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>[CH3:26][O:25][C:16]1[CH:15]=[C:14]([CH:10]([N+:11]#[C-:12])[S:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:27])=[CH:6][CH:5]=2)(=[O:8])=[O:9])[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[C:17]=1[O:23][CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 46938501HCID 46938501, compound

Product 1

HCID 46938504HCID 46938504, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

Compound 3c (2.63 g, 6.68 mmol) was suspended in dry DME (100 mL) and cooled to −10° C. POCl3 (3.78 mL, 40.4 mol) was added and a mixture of Et3N (7.5 mL, 66.6 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 yellow solid crystallized from the residue, which was collected and dried in vacuum. Yield: 520 mg (1.51 mmol, 23%); yellow solid of mp 134° C. (dec.); νmax (ATR)/cm−1 2949, 2140, 1593, 1538, 1494, 1453, 1360, 1337, 1315, 1285, 1248, 1184, 1156, 1145, 1082, 1065, 988, 921, 819, 784, 701, 667; 1H NMR (300 MHz, CDCl3) δ 2.48 (3H, s), 3.91 (3H, s), 4.00 (3H, s), 5.53 (1H, s), 7.12 (1H, d, J=2.2 Hz), 7.18 (1H, d, J=2.2 Hz), 7.38 (2H, d, J=8.4 Hz), 7.67 (2H, d, J=8.4 Hz); 13C NMR (75.5 MHz, CDCl3) 821.9, 56.7, 62.3, 75.3, 115.3, 116.3, 122.3, 129.7, 129.8, 130.4, 144.6, 144.8, 147.4, 154.4, 167.5; m/z (EI) 375 (6) [M+-1], 344 (12), 278 (23), 262 (22), 221 (100), 211 (47), 155 (32), 139 (38).

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 yellow solid crystallized from the residue, which
  8. customwas collected
  9. customdried in vacuum

Sources & evidence

ORD record
ord-dad6439b4617455d94520e29d0679486
Source dataset
uspto-grants-2015_03
Patent number
US08980933B2

Reaction notes

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