4-Nitro-5,6,7,8-tetrahydronaphth-1-yl isothiocyanate → 2-(4-Nitro-5,6,7,8-tetrahydro-1-naphthylimino)-3-thia-1-azaspiro[4.4]nonane
Reaction equation
Cl.[NH2:2][C:3]1([CH2:8]Cl)[CH2:7][CH2:6][CH2:5][CH2:4]1.[N+:10]([C:13]1[C:22]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=2[C:16]([N:23]=[C:24]=[S:25])=[CH:15][CH:14]=1)([O-:12])=[O:11]>>[N+:10]([C:13]1[C:22]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=2[C:16]([N:23]=[C:24]2[S:25][CH2:8][C:3]3([CH2:7][CH2:6][CH2:5][CH2:4]3)[NH:2]2)=[CH:15][CH:14]=1)([O-:12])=[O:11]Participants
Procedure
1-Amino-5,6,7,8-tetrahydronaphthaline was converted to 1-acetamino-5,6,7,8-tetrahydronaphthaline according to Method A2a, Step 1. The acetanilide was converted to 1-acetamino-4-nitro-5,6,7,8-tetrahydronaphthaline according according to Method A2a, Step 2. The acetanilide was deprotected according to Method A2a, Step 3 to give 1-amino-4-nitro-5,6,7,8-tetrahydronaphthaline. The aniline was converted to 4-nitro-5,6,7,8-tetrahydro-1-naphthyl 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 4-nitro-5,6,7,8-tetrahydro-1-naphthyl isothiocyanate according to Method C1a to give 2-(4-nitro-5,6,7,8-tetrahydro-1-naphthylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with isobutyl bromide according to Method D2a to afford 1-isobutyl-2-(4-nitro-5,6,7,8-tetrahydro-1-naphthylimino)-3-thia-1-azaspiro[4.4]nonane.
Sources & evidence
- ORD record
- ord-02ebe1045fa1432eaa0ebd28e341fa3d
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353006B1
Reaction notes
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