Ammonia → HCID 135674607, compound

HRID 280277Notes

Reaction equation

HRID 280277 reaction equation
C(N1C=CN=C1)([N:3]1C=CN=C1)=O.[Cl:13][C:14]1[CH:15]=[C:16]([CH3:35])[C:17]([OH:34])=[C:18]([C:20](=[N:28][CH2:29][CH2:30][C:31](O)=[O:32])[C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[CH:19]=1.N>O1CCCC1>[Cl:13][C:14]1[CH:15]=[C:16]([CH3:35])[C:17]([OH:34])=[C:18]([C:20](=[N:28][CH2:29][CH2:30][C:31]([NH2:3])=[O:32])[C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[CH:19]=1

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 682631,1'-CarbonyldiimidazoleHCID 135674613HCID 135674613, compound

Product 1

HCID 135674607HCID 135674607, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a hood, carbonyldiimidazole (5.56 g; 0.0312 mol) is added gradually to a stirred solution of the acid obtained in Example 1 (11 g; 0.0312 mol) in 150 ml of dry tetrahydrofuran. The stirring is continued for 11/2 hours at ambient temperature, and the solution is then poured into 100 ml of liquid NH3 and the whole is stirred until the evaporation of the ammonia has ended (about 3 hours). The residue is evaporated to dryness in vacuo. The residue is dissolved in CH2Cl2 and the methylene chloride solution is washed with water and with a saturated solution of sodium bicarbonate and then dried over MgSO4. Evaporation gives a solid, which is chromatographed on a column (SiO2, AcOEt). The solid obtained is recrystallised from AcOEt (i.e. ethyl acetate) to give a yellow solid.

Workup

  1. custom2 hours
  2. customat ambient temperature
  3. custom(about 3 hours)
  4. customThe residue is evaporated to dryness in vacuo
  5. dissolutionThe residue is dissolved in CH2Cl2
  6. washthe methylene chloride solution is washed with water and with a saturated solution of sodium bicarbonate
  7. dry with materialdried over MgSO4
  8. customEvaporation
  9. customgives a solid, which
  10. customis chromatographed on a column (SiO2, AcOEt)
  11. customThe solid obtained
  12. customis recrystallised from AcOEt (i.e. ethyl acetate)
  13. customto give a yellow solid

Sources & evidence

ORD record
ord-c9c1e67faf1c44659c46fd346d6c369b
Source dataset
uspto-grants-1986_05
Patent number
US04588748

Reaction notes

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