2-Chloroethylamine → HCID 18316035, compound

HRID 276328Notes

Reaction equation

Cl[CH2:2][CH2:3][NH2:4].[CH3:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[N:15]=[C:16]=[S:17]>>[CH3:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[N:15]=[C:16]1[N:4]([CH:11]2[CH2:10][CH2:9][CH2:8][CH:7]=[CH:6]2)[CH2:3][CH2:2][S:17]1

Participants

Reactant 2

HCID 133692-Chloroethylamine

HCID 1456212-Methyl-4-nitrophenyl isothiocyanate

Product 1

HCID 18316035HCID 18316035, compound

Procedure

Cyclohex-2-en-1-one was reduced according to Method B2b, Step 1 to afford cyclohex-2-en-1-ol. The alcohol was converted to the 3-bromo-1-cyclohexene according to Method B2b, Step 2. The halide was converted to N-(cyclohex-2-en-1-yl)-N-(2-hydroxyethyl)amine according to Method B2b, Step 3. The alcohol was reacted with SOCl2 according to Method B7a to afford N-(cyclohex-2-en-1-yl)-N-(2-chloroethyl)ammmonium chloride. The chloroethylamine was reacted with 2-methyl-4-nitrophenyl isothiocyanate according to method C1a to afford 2-(2-methyl -4-nitrophenylimino)-3-(cyclohex-2-en-1-yl)-1,3-thiazolidine.

Sources & evidence

ORD record: ord-1039ae2380d84ec8b17c94f8d6d566bf
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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