Imidazole → HCID 59144079, compound

HRID 424552Notes

Reaction equation

HRID 424552 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:25]I.[NH2:27][C:28]1[CH:33]=[C:32]([N+:34]([O-:36])=[O:35])[CH:31]=[CH:30][C:29]=1[S:37][CH2:38][CH2:39]O>C1COCC1.C(OCC)(=O)C>[I:25][CH2:39][CH2:38][S:37][C:29]1[CH:30]=[CH:31][C:32]([N+:34]([O-:36])=[O:35])=[CH:33][C:28]=1[NH2:27]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 591441672-(2-Amino-4-nitrophenylthio)ethanol

Product 1

HCID 59144079HCID 59144079, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of triphenylphosphine (1.81 g, 6.93 mmol) and imidazole (1.887 mL, 13.86 mmol) in THF (15 mL) at 0° C. was added iodine (1.759 g, 6.93 mmol). After stirring for 5 minutes, 2-(2-amino-4-nitrophenylthio)ethanol (990 mg, 4.62 mmol) was added as a solution in THF (5 mL). The resulting mixture was stirred at 0° C. for 1 hour, then diluted with ethyl acetate and washed with water (3×) and brine. The organic phase was dried, filtered, and concentrated then chromatographed in 4:1 hexanes:ethyl acetate giving the desired compound (1.18 g, 79%) as an orange solid. 1H NMR (DMSO-d6) δ 7.55 (d, J=2.4 Hz, 1H), 7.45 (d, J=8.4 Hz, 1H), 7.34 (dd, J=8.4, 2.4 Hz, 1H), 5.89 (brs, 2H), 3.38-3.26 (m, 4H); EI-MS (m/z, %): 324 (M+, 46), 196 (81), 154 (100), 126 (95).

Workup

  1. stirringThe resulting mixture was stirred at 0° C. for 1 hour
  2. washwashed with water (3×) and brine
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthen chromatographed in 4:1 hexanes

Sources & evidence

ORD record
ord-618ae62b034d447f9517fad144635c92
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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