1-Propanol → Ammonia

HRID 2186761Notes

Reaction equation

HRID 2186761 reaction equation
[Na].[CH2:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)(=[O:13])=[O:12])=[CH:7][C:6]=1[C:21]1[NH:22][C:23](=[O:38])[C:24]2[C:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:28][N:27]([CH2:36][CH3:37])[C:25]=2[N:26]=1)[CH3:3].[CH2:39](O)CC>>[NH3:14].[CH2:36]([N:27]1[C:25]2[N:26]=[C:21]([C:6]3[CH:7]=[C:8]([S:11]([N:14]4[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]4)(=[O:12])=[O:13])[CH:9]=[CH:10][C:5]=3[O:4][CH2:2][CH2:3][CH3:39])[NH:22][C:23](=[O:38])[C:24]=2[C:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[N:28]1)[CH3:37]

Participants

5

Reactant 3

HCID 10311-Propanol3×HCID 5360545Sodium2×HCID 135544191HCID 135544191, compound

Product 2

HCID 222AmmoniaHCID 135536953HCID 135536953, compound

Procedure

A suspension of sodium (25 mg, 1.1 mmol) in n-propanol (1 ml) was added to the title compound of example 6 (80 mg, 0.15 mmol) in n-propanol (1 ml), and the reaction mixture heated under reflux for 72 hours. Further sodium (100 mg, 4.34 mmol) and n-propanol (5 ml) were added portionwise over a further 48 hours, then the mixture cooled and evaporated under reduced pressure. The residue was purified by preparative thin layer chromatography on silica gel, using dichloromethane:methanol:0.88 ammonia (95:5:0.5) as eluant, to afford the title compound, (8 mg).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureunder reflux for 72 hours
  3. temperaturethe mixture cooled
  4. customevaporated under reduced pressure
  5. customThe residue was purified by preparative thin layer chromatography on silica gel

Sources & evidence

ORD record
ord-e2f2c1731c294d65b76d95905939eb6f
Source dataset
uspto-grants-2002_06
Patent number
US06407114B1

Reaction notes

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