Bromocyclopentane → HCID 18316538, compound

HRID 276546Notes

Reaction equation

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

Participants

Reactant 2

HCID 8728Bromocyclopentane

HCID 178436840HCID 178436840, compound

Product 1

HCID 18316538HCID 18316538, compound

Procedure

2- Ethylaniline was converted to 2-ethylacetanilide according to Method A2a, Step 1. The acetanilide was converted to 2-ethyl-4-nitroacetanilide according to Method A2a, Step 2. The acetanilide was deprotected according to Method A2a, Step 3 to give 2-ethyl-4-nitroaniline. The aniline was converted to 2-ethyl-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 with SOCl2 according to Method B7a to give 1-amino-1-(chloromethyl)cyclopentane HCl salt. The 2-chloroethylamine was reacted with 2-ethyl-4-nitrophenyl isothiocyanate according to Method C1a to give 2-(2-ethyl-4-nitrophenylimino)-1-thia-3-azaspiro[4.4]nonane. The thiazolidine was reacted with cyclopentyl bromide according to Method D2b to afford 3-cyclopentyl-2-(2-ethyl-4-nitrophenylimino)-1-thia-3-azaspiro[4.4]nonane.

Sources & evidence

ORD record: ord-3d5e48fe3d3549f5893f7b10929e8f64
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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