Triphenylphosphine → 5-Ethyloxy carbonylimidazo[2,1-b][1,3]thiazol-6-yl-methyl(triphenyl)phosphonium bromide

HRID 1882130Notes

Reaction equation

HRID 1882130 reaction equation
[Br:1][CH2:2][C:3]1[N:4]=[C:5]2[N:9]([C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:8]=[CH:7][S:6]2.[C:16]1([P:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[Br-:1].[CH2:14]([O:13][C:11]([C:10]1[N:9]2[C:5]([S:6][CH:7]=[CH:8]2)=[N:4][C:3]=1[CH2:2][P+:22]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:12])[CH3:15]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 68406302Ethyl 6-(bromomethyl)imidazo[2,1-b]thiazole-5-carboxylate

Product 1

HCID 866425275-Ethyloxy carbonylimidazo[2,1-b][1,3]thiazol-6-yl-methyl(triphenyl)phosphonium bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of Step 2 intermediate (1.90 g, 6.571 mmol) in acetonitrile (40 mL) was added triphenylphosphine (1.89 g, 7.228 mmol) at room temperature. The resulting reaction mixture was slowly heated to reflux overnight. The solvent was concentrated in vacuo and the residue was stirred with diisopropyl ether and filtered. The solid was dried under vacuum to afford 3.90 g of the product as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ 1.17 (t, J=7.2 Hz, 3H), 4.08 (q, J=6.9 Hz, 2H), 5.35 (s, 1H), 5.40 (s, 1H), 7.20-7.22 (m, 1H), 7.37 (br s, 1H), 7.50 (d, J=4.5 Hz, 1H), 7.68-7.76 (m, 10H), 7.81-7.87 (m, 3H), 7.99 (d, J=3.9 Hz, 1H); ESI-MS (m/z) 471.24 (MH)+.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas slowly heated
  3. temperatureto reflux overnight
  4. concentrationThe solvent was concentrated in vacuo
  5. filtrationfiltered
  6. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-e94140bda5b149a4bdad495260a129e6
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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