2,3-Dimethyl-4-nitrophenyl isothiocyanate → 2-(2,3-Dimethyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane

HRID 276564Notes

Reaction equation

HRID 276564 reaction equation
Cl.[NH2:2][C:3]1([CH2:8]Cl)[CH2:7][CH2:6][CH2:5][CH2:4]1.[CH3:10][C:11]1[C:16]([CH3:17])=[C:15]([N+:18]([O-:20])=[O:19])[CH:14]=[CH:13][C:12]=1[N:21]=[C:22]=[S:23]>>[CH3:10][C:11]1[C:16]([CH3:17])=[C:15]([N+:18]([O-:20])=[O:19])[CH:14]=[CH:13][C:12]=1[N:21]=[C:22]1[S:23][CH2:8][C:3]2([CH2:7][CH2:6][CH2:5][CH2:4]2)[NH:2]1

Participants

3

Reactant 2

HCID 183160152,3-Dimethyl-4-nitrophenyl isothiocyanateHCID 699924851-(Chloromethyl)cyclopentan-1-amine hydrochloride

Product 1

HCID 1784300782-(2,3-Dimethyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane

Procedure

2,3-Dimethyl-4-nitroaniline was synthesized as described in Method A4a. The aniline was converted into 2,3-dimethyl-4-nitrophenyl isothiocyanate as described in method A2d. 1-Amino-1-(hydroxymethyl)cyclopentane was synthesized as described in Method B1c. The 2-hydroxyethylamine was reacted with SOCl2 according to Method B7e to give 1-amino-1-(chloromethyl)cyclopentane HCl salt. The 2-chloroethylamine was reacted with 2,3-dimethyl-4-nitrophenyl isothiocyanate according to Method C1c to give 2-(2,3-dimethyl-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-486dbbc337614c329b6907c6e264c755
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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