Ammonia → HCID 67308882, compound

HRID 2041019Notes

Reaction equation

HRID 2041019 reaction equation
[CH3:1][C:2]([CH3:19])([C:11]#[C:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[NH3:20]>CCCCCC>[CH:12](=[C:11]1[C:2]([CH3:19])([CH3:1])[CH2:3][C:4]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[N:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 15306349HCID 15306349, compound

Product 1

HCID 67308882HCID 67308882, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

2-benzylidene-3,3-dimethyl-5-phenyl-3,4-dihydro-2H-pyrrole was prepared by reacting (3,3-dimethylpenta-1,4-diyne-1,5-diyl)dibenzene with ammonia in the presence of 10 mol % of catalyst E (165° C., 18 h). Compound 6f was the major product of the reaction (60%) which had a yield of 88%. Single crystals suitable for an X-ray diffraction study were obtained by slow evaporation of a hexane solution. mp: 101-103° C. (n-hexane) an Ortep diagram is shown in FIG. 6; 1H NMR (300 MHz, CDCl3) δ=1.37 (6H, s, CH3), 2.99 (2H, s, CH2), 5.98 (1H, s, CH), 7.24 (1H, t, J=7.4 Hz, CH), 7.41 (2H, t, J=7.7 Hz, CH), 7.49 (1H, d, J=1.3 Hz, CH), 7.51 (2H, d, J=2.3 Hz, CH), 8.05-8.10 (4H, m, CH); 13C NMR (75 MHz, CDCl3) δ=29.6 (CH3), 41.9 (Cq), 49.3 (CH2), 115.6 (CH), 126.5 (CH), 128.4 (CH), 128.4 (CH), 129.6 (CH), 131.3 (CH), 134.8 (Cq), 137.6 (Cq), 165.9 (NCqCH), 174.4 (N═CqCH2); HRMS (ESI): 262.1594 [(M+H)+, 262.1596 (C19H20N)].

Workup

  1. customthe major product of the reaction (60%) which

Sources & evidence

ORD record
ord-420c9916bf40444c90055b6b89e33c30
Source dataset
uspto-grants-2013_11
Patent number
US08580990B2

Reaction notes

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