Bromocyclopentane → 2-(2-Ethyl-4-nitrophenylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane

HRID 276605Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]=[C:19]1[S:23][CH2:22][C:21]2([CH2:27][CH2:26][CH2:25][CH2:24]2)[NH:20]1)[CH3:2].[CH:28]1(Br)[CH2:32][CH2:31][CH2:30][CH2:29]1>>[CH2:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]=[C:19]1[S:23][CH2:22][C:21]2([CH2:27][CH2:26][CH2:25][CH2:24]2)[N:20]1[CH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)[CH3:2]

Participants

Reactant 2

HCID 8728Bromocyclopentane

HCID 178436838HCID 178436838, compound

Product 1

HCID 183163612-(2-Ethyl-4-nitrophenylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane

Procedure

2-Ethylaniline was protected as 2-ethylacetanilide according to Method A2a, Step 1. The acetamide was converted to 2-ethyl-4-nitroaniline, then deprotected according to Method A2a, Step 2. The aniline was converted to 2-ethyl-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 2-ethyl-4-nitrophenyl isothiocyanate according to Method C1e to give 2-(2-ethyl-4-nitrophenylphenylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with cyclopentyl bromide according to Method D2b to give 2-(2-ethyl-4-nitrophenylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane.

Sources & evidence

ORD record: ord-8d60472fa733483fbd67c6e18180f39e
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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