Iodoethane → HCID 178477466, compound

HRID 723966Notes

Reaction equation

HRID 723966 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]2[S:12][C:13]3[CH:19]=[C:18]([NH:20][C:21]([NH2:23])=[S:22])[CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:4][CH:3]=1.[CH2:24](I)[CH3:25]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]2[S:12][C:13]3[CH:19]=[C:18]([NH:20][C:21](=[NH:23])[S:22][CH2:24][CH3:25])[CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6340IodoethaneHCID 10046967HCID 10046967, compound

Product 1

HCID 178477466HCID 178477466, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

{2-[2-(4-Bromo-phenyl)-ethylamino]-benzothiazol-6-yl}-thiourea (Example 39, 51.3 mg, 0.126 mmol) was dissolved in dry DMF (0.5 mL). Ethyl iodide (11 μl, 1.1 eq) was added and the yellow solution stirred at room temperature for 23 hours. The solution was diluted with ethyl acetate (10 mL) and extracted with ice water (2 mL) followed by ice cold brine (3×2 mL). The product was dried over MgSO4, filtered and concentrated to give a yellow oil. The product was purified by chromatography on silica gel (5% 2M ammonia/methanol in CH2Cl2) to give the isothiourea (12.5 mg, 23%). The product was dissolved in methanol (1.0 mL) and acidified with 1.0 M HCl in ether (4 mL). The orange precipitate was collected by filtration and washed with hexanes (6.0 mg, 10%). MS (M+1, 435, 437).

Workup

  1. extractionextracted with ice water (2 mL)
  2. dry with materialThe product was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a yellow oil
  6. customThe product was purified by chromatography on silica gel (5% 2M ammonia/methanol in CH2Cl2)

Sources & evidence

ORD record
ord-4559b11baa6f42ba96e81c3bf144bc03
Source dataset
uspto-grants-2006_11
Patent number
US07141595B2

Reaction notes

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