Benzene → HCID 11487168, compound

HRID 2213169Notes

Reaction equation

HRID 2213169 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:26][CH2:27][C:28]#[CH:29])[C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]#[CH:23])=[C:16]([O:24][CH3:25])[CH:15]=2)=O)=[CH:4][CH:3]=1.C1C=CC=CC=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:45]2)=CC=1>C(OCC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:26][CH2:27][C:28]#[CH:29])[C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]#[CH:23])=[C:16]([O:24][CH3:25])[CH:15]=2)=[S:45])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 87949Lawesson's reagentHCID 11292824Mandipropamid

Product 1

HCID 11487168HCID 11487168, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-(4-Chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-(prop-2-ynyloxy)-acetamide (0.822 g) and benzene (30 ml) are stirred at +55° C. 2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (“Lawesson's reagent”; 1.61 g) is added. The reaction mixture is stirred for additional 7 hours at +55° C. to +60° C. After cooling to room temperature diethylether (100 ml) is added. The mixture is then filtered. The solvent of the filtrate is evaporated. 2-(4-Chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-(prop-2-ynyloxy)-thioacetamide is obtained which is purified by flash-column-chromatography on silica gel using ethyl acetate/hexane. The purified product is in form of a resin. 1H-NMR (300 MHz, CDCl3, δ(ppm)): 2.45–2.55(m, 2H), 2.95(t, 2H), 3.85(s, 3H), 3.9–4.2(m, 4H), 4.75(d, 2H), 5.35(s, 1H), 6.65–6.8(m, 2H), 7.0(d, 1H), 7.2–7.4(m, 4H), 8.4–8.6(m, 1H).

Workup

  1. additionis added
  2. filtrationThe mixture is then filtered
  3. customThe solvent of the filtrate is evaporated

Sources & evidence

ORD record
ord-18a19e10b3574480a79975c77082096b
Source dataset
uspto-grants-2006_09
Patent number
US07105545B2

Reaction notes

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