Iodoethane → HCID 57837935, compound

HRID 732093Notes

Reaction equation

HRID 732093 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]=[C:11]([CH:13]([N:15]([CH:20]3[CH2:22][CH2:21]3)[C:16]([NH:18][CH3:19])=[S:17])[CH3:14])[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.I[CH2:24][CH3:25]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]=[C:11]([CH:13]([N:15]([CH:20]3[CH2:21][CH2:22]3)[C:16](=[N:18][CH3:19])[S:17][CH2:24][CH3:25])[CH3:14])[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 57837981HCID 57837981, compound

Product 1

HCID 57837935HCID 57837935, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-{1-[3-(3-Chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-ethyl}-1-cyclopropyl-3-methyl-thiourea (287 mg, 0.85 mmol) was mixed with iodoethane (484 mg, 3.4 mmol) in MeOH (5 mL) at 60° C. overnight. The reaction mixture was concentrated and basified with saturated sodium carbonate, then extracted with DCM. The organic layer was dried, concentrated to give the title compound (298 mg, 96 %). 1H-NMR: 8.11 (s, 1H), 8.01 (d, 1H), 7.51 (d, 1H), 7.46 (t, 1H), 5.51 (m, 1H), 3.27 (s, 3H), 2.85-3.00 (m, 2H), 2.60 (m, 1H), 1.79 (d, 3H), 1.30 (t, 3H), 0.83 (m)

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with DCM
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-674852c65b7046eca3247f9228a9b22c
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

Loading…