Triethylamine → 2-(4-Chlorobenzylthio)-5-nitrobenzo[d]oxazole

HRID 1896764Notes

Reaction equation

HRID 1896764 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10](=[S:12])[NH:9][C:8]=2[CH:13]=1)([O-:3])=[O:2].C(N(CC)CC)C.Br[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1>C(Cl)(Cl)Cl.C(OCC)(=O)C>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][S:12][C:10]2[O:11][C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:13][C:8]=3[N:9]=2)=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 7862935-Nitrobenzo[D]Oxazole-2-Thiol

Product 1

HCID 673325842-(4-Chlorobenzylthio)-5-nitrobenzo[d]oxazoleYield 78%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 5-nitrobenzo[d]oxazole-2(3H)-thione (196.2 mg, 1.0 mmol) in chloroform (10 mL) was added triethylamine (278 μL, 2 mmol) followed by 1-(bromomethyl)-4-chlorobenzene (226 mg, 1.1 mmol). The reaction was stirred at 60° C. for 2 h. After cooling, the reaction was diluted with ethyl acetate, washed with dilute aqueous hydrochloric solution and brine. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting solid was purified by column chromatography eluting with ethyl acetate/hexanes 1:10 v/v to afford 250 mg (78%) of the title compound (LCMS RT=7.64 min)

Workup

  1. temperatureAfter cooling
  2. washwashed with dilute aqueous hydrochloric solution and brine
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. customevaporated
  5. customThe resulting solid was purified by column chromatography
  6. washeluting with ethyl acetate/hexanes 1:10 v/v

Sources & evidence

ORD record
ord-f8a300d4dc894f7ab4a38ff306059c8e
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

Loading…