1-Methylimidazole → HCID 178480884, compound

HRID 72105Notes

Reaction equation

HRID 72105 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1.[Br-:7].[Br:8][CH2:9][CH2:10][CH2:11][P+:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[Br-:8].[CH3:1][N:2]1[CH:6]=[CH:5][N+:4]([CH2:9][CH2:10][CH2:11][P+:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:3]1.[Br-:7]

Participants

4

Reactant 2

HCID 13901-MethylimidazoleHCID 2723862(3-Bromopropyl)triphenylphosphonium bromide

Product 1

HCID 178480884HCID 178480884, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Methyl-3-(3-(triphenylphosphonio)propyl)-1H-imidazol-3-ium bromide was synthesized by refluxing the mixture of 1-methyl-1H-imidazole and (3-bromopropyl)triphenylphosphonium bromide (1:1) in ethanol for 12 h; after cooling down, the solvent was removed and the crude product was washed with ethyl acetate. Then the white product was treated with silver (I) oxide in CH2Cl2 for 12 h, and the crude Ag—NHC product was filtered and washed with CH2Cl2 and then with diethyl ether, and was used for the next step directly. The procedure for the synthesis of 3 is similar to that for 1. Total yield 32%; 1H NMR (400 MHz, CD3CN, 25° C.): δ=8.21 (t, J=8.0 Hz, 1H), 7.82 (m, 3H), 7.69-7.72 (m, 3H), 7.66 (d, J=2.0 Hz, 1H), 7.55-7.63 (m, 12H), 7.17 (d, J=0.9 Hz, 2H), 6.98 (d, J=0.9 Hz, 2H), 4.57 (t, J=7.1 Hz, 2H), 3.94 (s, 3H), 3.27 (m, 2H), 2.11 (m, 2H); FAB-MS: m/z 940 [M−OTf]+; Elemental Analysis calcd (%) for C38H33AuF6N7O6PS2.H2O: C, 41.20; H, 3.18; N, 8.85; found: C, 41.25; H, 3.29; N, 8.72.

Workup

  1. temperatureby refluxing
  2. temperatureafter cooling down
  3. customthe solvent was removed
  4. washthe crude product was washed with ethyl acetate
  5. additionThen the white product was treated with silver (I) oxide in CH2Cl2 for 12 h
  6. filtrationthe crude Ag—NHC product was filtered
  7. washwashed with CH2Cl2
  8. customThe procedure for the synthesis of 3

Sources & evidence

ORD record
ord-b70bb68c652c4c4b9c8bad8b464be0b1
Source dataset
uspto-grants-2014_09
Patent number
US08828984B2

Reaction notes

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