1-Bromo-2-methylpropane → 1-Isobutyl-2-(2-isopropyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane
Reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[N:13]=[C:14]1[S:18][CH2:17][C:16]2([CH2:22][CH2:21][CH2:20][CH2:19]2)[NH:15]1)([CH3:3])[CH3:2].[CH2:23](Br)[CH:24]([CH3:26])[CH3:25]>>[CH2:23]([N:15]1[C:16]2([CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:17][S:18][C:14]1=[N:13][C:5]1[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=1[CH:1]([CH3:3])[CH3:2])[CH:24]([CH3:26])[CH3:25]Participants
Procedure
2-Isoropylaniline was converted to 2-isopropylacetanilide according to Method A2a, Step 1. The acetanilide was converted to 2-isopropyl-4-nitroacetanilide according to Method A2a, Step 2. The acetanilide was deprotected according to Method A2a, Step 3 to give 2-isopropyl-4-nitroaniline. The aniline was converted to 2-isopropyl-4-nitrophenyl isothiocyanate according to Method A2a, Step 3. 1-Amino-1-(hydroxymethyl)cyclopentane was synthesized as described in Method B1c. The 2-hydroxyethylamine was reacted with SOCl2 according to Method B7a to give 1-amino-1-(chloromethyl)cyclopentane HCl salt. The 2-chloroethylamine was reacted with 2-isopropyl-4-nitrophenyl isothiocyanate according to Method C1a to give 2-(2-isopropyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with isobutyl bromide according to Method D2a to afford 1-isobutyl-2-(2-isopropyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane.
Sources & evidence
- ORD record
- ord-8f089619835748b3bf011a0d01569201
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353006B1
Reaction notes
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