Thionyl Chloride → HCID 178428745, compound

HRID 276507Notes

Reaction equation

[NH2:1][CH:2]([CH2:5]O)[CH2:3]O.O=S(Cl)[Cl:9].[CH3:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[N:21]=[C:22]=[S:23]>>[CH3:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[N:21]=[C:22]1[NH:1][CH:2]([CH2:5][Cl:9])[CH2:3][S:23]1

Participants

Reactant 3

HCID 24386Thionyl Chloride

HCID 68294Serinol

HCID 1456212-Methyl-4-nitrophenyl isothiocyanate

Product 1

HCID 178428745HCID 178428745, compound

Procedure

2-Amino-1,3-propanediol was reacted with excess SOCl2 followed by 2-methyl-4-nitrophenyl isothiocyanate according to Method C2a to give 2-(2-methyl-4-nitrophenylimino)-4-(chloromethyl)-1,3-thiazolidine. The thiazolidine was reacted with dimethylamine according to Method D13a to give 2-(2-methyl-4-nitrophenylimino)-4-(N-isobutyl-N-methylaminomethyl)-1,3-thiazolidine, which was reacted with isobutyl bromide according to Method D2a to afford 2-(2-methyl-4-nitrophenylimino)-3-isobutyl-4-(N,N-dimethylaminomethyl)-1,3-thiazolidine.

Sources & evidence

ORD record: ord-79d7194882d34b8f9c28f62522b45a42
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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