Phosphorus sulfide (P2S5) → HCID 9966456, compound

HRID 277880Notes

Reaction equation

HRID 277880 reaction equation
[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[CH:13]=[C:14]([CH:17]=[C:18]([F:20])[CH:19]=3)[C:15]#[N:16])[CH:10]=2)[NH:5][C:4](=O)[CH2:3]1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:24]>N1C=CC=CC=1>[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[CH:13]=[C:14]([CH:17]=[C:18]([F:20])[CH:19]=3)[C:15]#[N:16])[CH:10]=2)[NH:5][C:4](=[S:24])[CH2:3]1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 99007433-(4,4-Dimethyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-5-fluorobenzonitrile

Product 1

HCID 9966456HCID 9966456, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Prepared by heating under reflux overnight a stirred mixture of 3-(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-5-fluorobenzonitrile and an equal weight of phosphorus pentasulfide in pyridine and workup as in the previous example gave a yellow solid: mp. 240-242° C. dec.; 1H-NMR (DMSO-d6) δ 12.37 (s, 1H), 8.13 (s, 1H), 7.98 (dt, 1H, J=10.4 and 5.4 Hz), 7.81 (d, 1H, J=8.4 Hz), 7.7 (d, 1H, J=1.8 Hz), 7.68 (dd, 1H, J=8.3 and 1.9 Hz), 7.22 (d, 1H, J=8.3 Hz), 2.85 (s, 2H), 1.27 (s, 6H); MS m/z 309 [M−H]− Anal. Calc. For C18H15FN2S 0.10 H2O: C, 69.25, H, 4.91, N, 8.97. Found: C, 69.15, H, 4.74, N, 8.75.

Workup

  1. customPrepared
  2. temperatureby heating
  3. temperatureunder reflux overnight

Sources & evidence

ORD record
ord-e11a019a9fcb48109b548ecdaff76ca8
Source dataset
uspto-grants-2002_03
Patent number
US06358948B1

Reaction notes

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