Water → HCID 86671865, compound

HRID 2199580Notes

Reaction equation

HRID 2199580 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][CH:9]([C:11]2[S:12][CH:13]=[C:14]3[O:19][CH2:18][CH2:17][O:16][C:15]=23)O)[CH:5]=[CH:4][N:3]=1.O=P(Cl)(Cl)Cl.O>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]=[CH:9][C:11]2[S:12][CH:13]=[C:14]3[O:19][CH2:18][CH2:17][O:16][C:15]=23)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 86671864HCID 86671864, compound

Product 1

HCID 86671865HCID 86671865, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-78 °C

Procedure

Compound (9) (800 mg, 2.34 mmol) was dissolved in pyridine (2 mL). POCl3 (327 μL, 538 mg, 3.51 mmol) was added and the resulting mixture was cooled to −78° C. Upon addition of water (40 mL) the formation of a precipitate was observed. The cooling bath was removed and the mixture was stirred for 15 min. A precipitate was obtained which was collected upon filtration and washed with petroleum ether/ethyl acetate (20 mL, 1:1) affording pure (10) as a yellow solid (380 mg, 1.17 mmol, 50%), mp 127-129° C. 1H NMR (500 MHz, CDCl3) δ 8.27 (d, J=5.2 Hz, 1H), 7.51 (s, 1H), 7.34 (d, J=16.1 Hz, 1H), 7.25 (d, J=5.2 Hz, 1H), 6.70 (d, J=16.1 Hz, 1H), 6.38 (s, 1H), 4.35-4.33 (m, 2H), 4.27-4.25 (m, 2H).

Workup

  1. customThe cooling bath was removed
  2. customA precipitate was obtained which
  3. filtrationwas collected upon filtration
  4. washwashed with petroleum ether/ethyl acetate (20 mL, 1:1)

Sources & evidence

ORD record
ord-d3584db605f742359c0005f387016172
Source dataset
uspto-grants-2016_06
Patent number
US09359334B2

Reaction notes

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