1-Butanol → HCID 86587668, compound

HRID 1937718Notes

Reaction equation

HRID 1937718 reaction equation
C([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]/[CH:25]=[CH:26]\[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH2:35])CCCCCCCCCCCCCCC.[N:36]#[C:37][NH2:38].[CH2:39](O)[CH2:40][CH2:41][CH3:42]>C(Cl)Cl>[CH2:42]([N:35]([CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]/[CH:26]=[CH:25]\[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17])[C:37](=[NH:38])[NH2:36])[CH2:41][CH2:40][CH2:39][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 9864CyanamideHCID 86587667HCID 86587667, compound

Product 1

HCID 86587668HCID 86587668, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

The mixture of a hydrochloride salt of 1 (285 mg, 0.54 mmol), cyanamide (50 mg, 1.19 mmol) and 1-butanol (2 ml) was stirred at 120° C. for 2 hours. The cooled mixture was diluted with CH2Cl2(50 ml) and washed with saturated aqueous NaCl(Brine)/methanol 1:1 (50 ml). The organic layer was then dried (Na2SO4), evaporated to an oil and chromatographed on a column of silica gel using CH2Cl2/methanol/conc. NH4OH 40:10:2 giving 80 mg of the desired material (yield, 28%). 1H NMR (CDCl3) d 7.08 (br s, 1H, NH), 5.34 (m, 2H, CH═CH), 3.29 (m, 4H), 2.00 (m, 4H), 1.62 (m, 4H), 1.25 (m, 48H), 0.88 (m, 6H). FAB-MS: 535 [M+H]+.

Workup

  1. washwashed with saturated aqueous NaCl(Brine)/methanol 1:1 (50 ml)
  2. dry with materialThe organic layer was then dried (Na2SO4)
  3. customevaporated to an oil
  4. customchromatographed on a column of silica gel

Sources & evidence

ORD record
ord-7103bf5d34ca4dc39c27866f5cd5fb9d
Source dataset
uspto-grants-2002_05
Patent number
US06395713B1

Reaction notes

Loading…