Sodium Bicarbonate → 1-Cyclopentyl-2-(2-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane

HRID 276290Notes

Reaction equation

HRID 276290 reaction equation
Cl.[CH:2]1([N:7]2[C:11]3([CH2:15][CH2:14][CH2:13][CH2:12]3)[CH2:10][S:9][C:8]2=[N:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=2[CH3:26])[CH2:6][CH2:5][CH2:4][CH2:3]1.C([O-])(O)=O.[Na+]>O.CCOC(C)=O>[CH:2]1([N:7]2[C:11]3([CH2:15][CH2:14][CH2:13][CH2:12]3)[CH2:10][S:9][C:8]2=[N:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=2[CH3:26])[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 699929501-cyclopentyl-2-(2-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane HCl salt

Product 1

HCID 99507321-Cyclopentyl-2-(2-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonaneYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1-cyclopentyl-2-(2-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane HCl salt (Method C6b; 52.4 g, 0.132 mol) dissolved in a mixture of water (300 mL) and EtOAc (500 mL) wag added NaHCO3 (15 g, 0.178 mol, 1.3 equiv.). The mixture was stirred for 1 h and the resulting organic layer was dried (MgSO4) concentrated under reduced pressure. The resulting light yellow solid was treated with EtOH (100 mL), and concentrated under reduced pressure twice to give 1-cyclopentyl-2-(2-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane (46 g, 97%): mp 111-112° C.; 1H NMR (CDCl3) δ1.49-1.53 (m, 2H), 1.63-1.80 (m, 8H), 1.81-1.91 (m, 4H), 2.21 (s, 3H), 3.02 (s, 2H), 3.60-3.70 (m, 1H), 6.87 (d J=8.5 Hz, 1H), 8.02 (m, 2H), CI-MS m/z 360 ((M+H)+).

Workup

  1. dry with materialthe resulting organic layer was dried (MgSO4)
  2. concentrationconcentrated under reduced pressure
  3. additionThe resulting light yellow solid was treated with EtOH (100 mL)
  4. concentrationconcentrated under reduced pressure twice

Sources & evidence

ORD record
ord-29c9e13126904f01ab4da57ab1d6e854
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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