Bromocyclopentane → 2-(3-Methyl-4-nitrophenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:11]=[C:12]2[S:16][CH2:15][C:14]3([CH2:20][CH2:19][CH2:18][CH2:17]3)[NH:13]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH:21]1(Br)[CH2:25][CH2:24][CH2:23][CH2:22]1>>[CH3:1][C:2]1[CH:3]=[C:4]([N:11]=[C:12]2[S:16][CH2:15][C:14]3([CH2:17][CH2:18][CH2:19][CH2:20]3)[N:13]2[CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]Participants
3
Procedure
3-Methyl-4-nitroaniline was converted to 3-methyl-4-nitrophenyl isothiocyanate according to Method A2a, Step 3. 1-Hydroxymethylcyclopentanamine was prepared according to Method B1c. The 2-hydroxyethylamine was converted to 1-chloromethylcyclopentanamine HCl salt according to Method B7e. 1-Chloromethylcyclopentanamine HCl salt was reacted with 3-methyl-4-nitrophenyl isothiocyanate according to Method C1e to give 2-(3-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with cyclopentyl bromide according to Method D2b to give 2-(3-methyl-4-nitrophenylimino)-1-cyclopentyl-3-thia-1-azaspiro [4.4]nonane.
Sources & evidence
- ORD record
- ord-66212e62354c4c1eba9cca6020bbdce6
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353006B1
Reaction notes
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