Phosphorus sulfide (P2S5) → HCID 178516009, compound

HRID 539556Notes

Reaction equation

HRID 539556 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][CH2:19][C:20]3[N:21]=[N:22][NH:23][CH:24]=3)=[C:9]([OH:25])[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:28].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][CH2:19][C:20]3[N:21]=[N:22][NH:23][CH:24]=3)=[C:9]([OH:25])[C:8]2=[S:28])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 178515982HCID 178515982, compoundHCID 178516893HCID 178516893, compound

Product 1

HCID 178516009HCID 178516009, compoundYield 86.2%

Procedure

Reaction of 159f (0.12 g, 0.532 mmol) and P4S10 (0.076 g, 0.17 mmol) under neat conditions as described for synthesis of 162b gave compound 162f (0.054 g, 43%) as a olive green semi-solid. 1H NMR (400 MHz, DMSO) δ 8.55 (m, 1H), 7.81 (d, J=8.2 Hz, 2H), 7.65 (d, J=6.2 Hz, 1H), 7.42 (m, 2H), 7.30 (m, 1H), 7.02 (m, 1H), 6.85 (m, 1H), 4.50 (m, 2H), 4.36 (t, J=7.1 Hz, 2H), 1.85 (d, J=7.0 Hz, 4H), 1.33 (s, 6H). 13C NMR (100 MHz, CDCl3) δ 147.76, 130.66, 128.76, 130.39, 128.98, 128.80, 128.06, 125.97, 125.67, 119.46, 60.10, 50.25, 30.11, 29.67, 28.33, 26.13, 26.10. HRMS (FAB) calcd for C20H25N4OS [M+H]+ 369.174. found 369.1762.

Sources & evidence

ORD record
ord-7cf7d268e41d4d4eb138be4b4a620e72
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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