Stannous chloride dihydrate → 4-(benzylsulfanyl)aniline

HRID 2185455Notes

Reaction equation

HRID 2185455 reaction equation
O.O.[Sn](Cl)Cl.[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([S:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)([O-])=O>C(O)C.C(OCC)(=O)C>[CH2:16]([S:15][C:12]1[CH:11]=[CH:10][C:9]([NH2:6])=[CH:14][CH:13]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 14855761-(benzylsulfanyl)-4-nitrobenzene

Product 1

HCID 50841454-(benzylsulfanyl)aniline

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

Tin (II) chloride dihydrate (444 mg) was added to a stirred solution of benzyl 4-nitrophenyl sulfide (A, 704 mg) in ethanol (20 mL). The mixture was stirred at 70° C. for 2 hr under nitrogen, allowed to cool down and then poured into ice. The pH was made slightly basic (pH 7-8). The mixture was diluted with ethyl acetate and washed with saturated sodium hydrogen carbonate and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound (565 mg) as a brown oil: 1H NMR (400 MHz, CDCl3) δ 3.59 (br s, 2H), 3.93 (s, 2H), 6.54-6.57 (m, 2H), and 7.11-7.26 (m, 7H).

Workup

  1. temperatureto cool down
  2. additionpoured into ice
  3. washwashed with saturated sodium hydrogen carbonate and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-21ef07f07fcc43ebbf944d269c993a7c
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

Loading…