Aniline → HCID 69319343, compound

HRID 2389500Notes

Reaction equation

HRID 2389500 reaction equation
C([O:5][C:6](=[O:21])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[S:17][CH2:18][CH2:19]Br)(C)(C)C.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CCO>[C:23]1([NH:22][CH2:19][CH2:18][S:17][C:9]2[N:8]([CH2:7][C:6]([OH:5])=[O:21])[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 90753832HCID 90753832, compound

Product 1

HCID 69319343HCID 69319343, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To tert-butyl[2-(2-bromo-ethylsulfanyl)-benzoimidazol-1-yl]-acetate (Intermediate 4-I, 25 mg, 0.065 mmol) in EtOH (0.7 ml) is added aniline (31.3 mg, 0.34 mmol). The resulting mixture is heated up to 70° C. for 1 h. After cooling the solvent is evaporated in vacuo and the crude ester is dissolved in TFA/dichloromethane (3:2, 2 ml) and stirred at rt for 2 h. Evaporation of the solvents in vacuo affords a crude product that is purified by chromatography on silica-gel (dichlromethane/MeOH, 100:7.5), yielding the pure title compound: tR=2.11 min (LC-2), ESI-MS (pos.): m/z 328.33 [M+H]+, ESI-MS (neg.): m/z 326.34 [M−H]+.

Workup

  1. temperatureAfter cooling the solvent
  2. customis evaporated in vacuo
  3. dissolutionthe crude ester is dissolved in TFA/dichloromethane (3:2, 2 ml)
  4. customEvaporation of the solvents in vacuo
  5. customaffords a crude product that
  6. customis purified by chromatography on silica-gel (dichlromethane/MeOH, 100:7.5)

Sources & evidence

ORD record
ord-27a843c49ffa4365ad78deb3489eff02
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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