Toluene → HCID 11983444, compound

HRID 2262752Notes

Reaction equation

HRID 2262752 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[C:9]([N:13]3[C:17]4[CH:18]=[CH:19][C:20]([CH:22](O)[CH3:23])=[CH:21][C:16]=4[N:15]=[CH:14]3)[CH:10]=[CH:11][CH:12]=2)=[N:4][CH:3]=1.C1(C)C=CC=CC=1.[N:32]12CCCN=C1CCCCC2.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1>[Cl:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[C:9]([N:13]3[C:17]4[CH:18]=[CH:19][C:20]([CH:22]([NH2:32])[CH3:23])=[CH:21][C:16]=4[N:15]=[CH:14]3)[CH:10]=[CH:11][CH:12]=2)=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 57572241HCID 57572241, compound

Product 1

HCID 11983444HCID 11983444, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

A stirred suspension of 1-{1-[3-(5-chloro-thiazol-2-yl)-phenyl]-1H-benzoimidazol-5-yl}-ethanol (1.0 g, 2.80 mmol) in a mixture anhydrous toluene (60 ml) and THF (10 ml) was cooled to 10° C. and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.5 ml, 3.36 mmol) and di-phenylphosphoryl azide (0.95 g, 3.36 mmol) were added, successively. Stirring was continued for 45 min at 10° C., whereafter the temperature was raised and the mixture was stirred at reflux for two days. The cooled mixture was concentrated in vacuo and the concentrate was partitioned between ethyl acetate and saturated, aqueous sodium carbonate. The organic extract was dried over magnesium sulphate, concentrated under reduced pressure and eluted through silica gel with a mixture of dichloro-methane, methanol and aqueous ammonia (9:1:0.1 v/v/v) to afford the desired product (0.75 g, 70%). LC-ESI-HRMS of [M+H]+ shows 355.079 Da. Calc. 355.07842 Da. dev. 1.6 ppm.

Workup

  1. temperaturewas raised
  2. stirringthe mixture was stirred
  3. temperatureat reflux for two days
  4. concentrationThe cooled mixture was concentrated in vacuo
  5. customthe concentrate was partitioned between ethyl acetate
  6. extractionThe organic extract
  7. dry with materialwas dried over magnesium sulphate
  8. concentrationconcentrated under reduced pressure
  9. washeluted through silica gel with a mixture of dichloro-methane, methanol and aqueous ammonia (9:1:0.1 v/v/v)

Sources & evidence

ORD record
ord-ddee9ae3421b409fa1b405c2d5669fec
Source dataset
uspto-grants-2010_12
Patent number
US07851490B2

Reaction notes

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