2-Butanamine, 2-methyl- → HCID 22402749, compound

HRID 260169Notes

Reaction equation

HRID 260169 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([NH:11][C:12](=[N:20][C:21]#[N:22])OC2C=CC=CC=2)[CH:7]=[C:8]([I:10])[CH:9]=1)=[N+:2]=[N-:3].[C:23]([NH2:28])([CH2:26][CH3:27])([CH3:25])[CH3:24]>C(O)(C)C>[N:1]([C:4]1[CH:5]=[C:6]([NH:11][C:12]([NH:20][C:21]#[N:22])=[N:28][C:23]([CH3:25])([CH3:24])[CH2:26][CH3:27])[CH:7]=[C:8]([I:10])[CH:9]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 689862-Butanamine, 2-methyl-HCID 178512287HCID 178512287, compound

Product 1

HCID 22402749HCID 22402749, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Step B-2. To a stirred suspension of N-(3-azido-5-iodophenyl)-N'-cyanocarbamimidic acid, phenyl ester (B-1, 1.09 g, 2.69 mmol) in isopropanol (20 mL) is added tert-amylamine (0.95 mL, 8.08 mmol). The reaction mixture is heated to reflux for 2.5 hour. The cooled reaction mixture is concentrated and the residue is diluted with ether (50 mL) and washed with 1 N aqueous sodium hydroxide (2×15 ml). The aqueous is extracted with ether (2×30 mL). The combined organics are dried (MgSO4), filtered and concentrated. The organic residue is purified by flash chromatography using 25% ethyl acetate in hexane as an eluent to afford 0.694 g of N-(3-azido-5-iodophenyl)-N'-cyano-N"-(1,1-dimethylpropyl)guanidine (B-2) as a foam. IR (mull) 3310, 3251, 3077, 2954, 2924, 2869, 2854, 2174, 2109, 1603, 1582, 1572, 1497, 1457, 1421, 1408, 1366, 1301, 1231, 844 cm-1 ; 1H NMR (CDCl3)δ8.29 (bs, 1 H), 7.33 (t, 1 H, J=2 Hz), 7.24 (t, 1 H, J=2 Hz), 6.83 (t, 1 H, J=2 Hz), 4.64 (bs I H), 1.70 (q, 2 H, J=7 Hz), 1.32 (s, 6 H), 0.84 (t, 3 H, J=7 Hz); 13C NMR (CDCl3) δ156.7, 142.7, 138.5, 129.0, 125.4, 116.9, 114.2, 94.8, 55.6, 32.9, 26.3, 8.1; Mass Spec (70eV, EI) m/z 397 (parent), 369, 328, 299, 258, 242, 232, 213, 172, 145, 130, 105, 71, 55, 43 (base); Exact mass calculated for C13H16IN7 : 397.0514. Found: 397.0532.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 2.5 hour
  3. customThe cooled reaction mixture
  4. concentrationis concentrated
  5. additionthe residue is diluted with ether (50 mL)
  6. washwashed with 1 N aqueous sodium hydroxide (2×15 ml)
  7. extractionThe aqueous is extracted with ether (2×30 mL)
  8. dry with materialThe combined organics are dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe organic residue is purified by flash chromatography

Sources & evidence

ORD record
ord-0dd12d8d6a0f4b7e81ddfc43c88b6392
Source dataset
uspto-grants-1996_06
Patent number
US05525742

Reaction notes

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