1-Iodopentane → HCID 53955720, compound

HRID 1977829Notes

Reaction equation

HRID 1977829 reaction equation
[Na].[C:2]([C:4]1[C:5]([S-:15])=[N:6][S:7][C:8]=1[NH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])#[N:3].I[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>O1CCCC1>[CH2:13]([O:12][C:10](=[O:11])[NH:9][C:8]1[S:7][N:6]=[C:5]([S:15][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:4]=1[C:2]#[N:3])[CH3:14]

Participants

5

Reactant 3

HCID 123351-IodopentaneHCID 5360545SodiumHCID 178473471HCID 178473471, compound

Product 1

HCID 53955720HCID 53955720, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of sodium, 4-cyano-5-ethoxycarbonylamino-isothiazole-3-thiolate (5.0 g, 20 mmol), 1-iodopentane (4.0 g, 20 mmol) and tetrahydrofuran (20 mL) was stirred at ambient temperature for 16 hours. After concentration in vacuo, the residue was partitioned between ethyl acetate and brine. The aqueous layer was extracted three times with ethyl acetate, and the combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The residue was filtered through a pad of silica gel using 1:1 ethyl acetate-hexane as eluent. The filtrated was concentrated and the residue was recrystallized from cold aqueous methanol, affording 2.5 g (42%) (4-cyano-3-pentylsulfanyl-isothiazol-5-yl)-carbamic acid ethyl ester as a colorless solid. An additional 0.5 g (8.4%) was obtained by concentration of the mother liquor and purification by radial chromatography (4 mm plate, 4:1 hexane-ethyl acetate). 1H NMR (400 MHz, acetone-d6) δ11.1 (bs, 1H), 4.32 (q, 2H, J=7.2 Hz), 3.21 (t, 2H, J=7.2 Hz), 1.73 (p, 2H, J=6.8 Hz), 1.44-1.28 (m, 7H), 0.90 (t, 3H, J=7.6 Hz) ppm; MS (APCI, m/z): 312 [M+Na]+.

Workup

  1. concentrationAfter concentration in vacuo
  2. customthe residue was partitioned between ethyl acetate and brine
  3. extractionThe aqueous layer was extracted three times with ethyl acetate
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. filtrationThe residue was filtered through a pad of silica gel using 1:1 ethyl acetate-hexane as eluent
  8. concentrationThe filtrated was concentrated
  9. customthe residue was recrystallized from cold aqueous methanol

Sources & evidence

ORD record
ord-8d8a21c99cfd4db6b13002583d0dc6fc
Source dataset
uspto-grants-2001_05
Patent number
US06235764B1

Reaction notes

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