1-Propanol → Ammonia

HRID 2085995Notes

Reaction equation

HRID 2085995 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[C:18]2[C:17](=[O:19])[NH:16][C:15]([C:20]3[CH:25]=[C:24]([S:26]([N:29]4[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]4)(=[O:28])=[O:27])[CH:23]=[CH:22][C:21]=3[O:36][CH2:37][CH3:38])=[N:14][C:13]=2[C:12]([CH2:39][CH2:40][CH3:41])=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:42](O)CC>>[NH3:10].[CH2:3]([N:10]1[C:18]2[C:17](=[O:19])[NH:16][C:15]([C:20]3[CH:25]=[C:24]([S:26]([N:29]4[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]4)(=[O:27])=[O:28])[CH:23]=[CH:22][C:21]=3[O:36][CH2:37][CH2:38][CH3:42])=[N:14][C:13]=2[C:12]([CH2:39][CH2:40][CH3:41])=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 10311-PropanolHCID 24758Sodium hydrideHCID 135740133HCID 135740133, compound

Product 2

HCID 222AmmoniaHCID 136425775HCID 136425775, compound

Procedure

A 60% w/w dispersion of sodium hydride in mineral oil (160 mg, 4 mmol) was added portionwise to stirred, ice-cooled propan-1-ol (20 ml). When the effervescence had ceased, the title compound of Example 41 (550 mg, 1 mmol) was added and the resulting mixture heated under reflux for 96 hours, then allowed to cool and evaporated under reduced pressure. The residue was partitioned between ethyl acetate (50 ml) and water (50 ml), then the separated aqueous phase extracted with ethyl acetate (100 ml in total). The combined organic solutions were dried (Na2SO4) and evaporated under reduced pressure, then the residue purified by column chromatography on silica gel, using ethyl acetate:methanol:0.880 aqueous ammonia (95:5:0.5) as eluant, to provide the title compound (230 mg) as a colourless foam. Found: C, 61.65; H, 6.48; N, 14.53. C29H36N6O4S requires C, 61.68; H, 6.48; N, 14.88%. δ (CDCl3): 0.98 (3H, t), 1.15 (3H, t), 1.83 (2H, m), 2.01 (2H, m), 2.24 (3H, s), 2.46 (4H, m), 2.92 (2H, t), 3.08 (4H, m), 4.22 (2H, t), 5.73 (2H, s), 7.12 (1H, d), 7.27 (3H, m), 7.36 (2H, m), 7.80 (1H, d), 8.82 (1H, s), 11.84 (1H, s). LRMS: m/z 565 (M+1)+.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureunder reflux for 96 hours
  3. temperatureto cool
  4. customevaporated under reduced pressure
  5. customThe residue was partitioned between ethyl acetate (50 ml) and water (50 ml)
  6. extractionthe separated aqueous phase extracted with ethyl acetate (100 ml in total)
  7. dry with materialThe combined organic solutions were dried (Na2SO4)
  8. customevaporated under reduced pressure
  9. customthe residue purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0f0ecb91269444f38c652bc158e22d51
Source dataset
uspto-grants-2004_04
Patent number
US06723719B1

Reaction notes

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