Phosphorus sulfide (P2S5) → HCID 178516004, compound

HRID 539555Notes

Reaction equation

HRID 539555 reaction equation
[C:1]1([N:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]3[N:20]=[N:21][NH:22][CH:23]=3)=[C:9]([OH:24])[C:8]2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:27].C1(N2C=CC(CCCC3N=NNC=3)=C(O)C2=S)C=CC=CC=1>>[C:1]1([N:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]3[N:20]=[N:21][NH:22][CH:23]=3)=[C:9]([OH:24])[C:8]2=[S:27])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 178515982HCID 178515982, compoundHCID 178516892HCID 178516892, compound

Product 1

HCID 178516004HCID 178516004, compoundYield 84.8%

Procedure

Reaction of 159e (0.18 g, 0.532 mmol) and P4S10 (0.118 g, 0.266 mmol) under neat conditions as described for synthesis of 162b gave compound 162e (0.080 g, 42%) as a olive green semi-solid. 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 7.83 (d, J=7.5 Hz, 2H), 7.76 (s, 1H), 7.41 (t, J=7.5 Hz, 2H), 7.32 (m, 2H), 6.94 (m, 1H), 6.72 (m, 1H), 4.49 (m, 2H), 4.40 (t, J=6.9 Hz, 2H), 1.97 (m, 4H), 1.36 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 164.38, 162.90, 147.70, 130.54, 128.76, 128.03, 126.64, 125.61, 119.51, 118.75, 118.29, 59.74, 50.10, 29.91, 27.99, 25.82, 25.65. HRMS (ESI) calcd for C19H23N4OS [M+H]+ 355.158. found 355.1632.

Sources & evidence

ORD record
ord-ec2b170609414ca49bccbb7a89ca7500
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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