Thionyl Chloride → HCID 178428755, compound

HRID 276492Notes

Reaction equation

[CH:1]([C@H:4]([NH2:7])[CH2:5]O)([CH3:3])[CH3:2].O=S(Cl)Cl.[CH3:12][C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=1[N:22]=[C:23]=[S:24]>>[CH3:12][C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=1[N:22]=[C:23]1[NH:7][C@@H:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][S:24]1

Participants

Reactant 3

HCID 24386Thionyl Chloride

HCID 1456212-Methyl-4-nitrophenyl isothiocyanate

HCID 640993L-Valinol

Product 1

HCID 178428755HCID 178428755, compound

Procedure

(1S)-1-Isopropyl-2-hydroxyethylamine was reacted with SOCl2 followed by 2-methyl-4-nitrophenyl isothiocyanate according to Method C2a to give (4S)-2-(2-methyl-4-nitrophenylimino)-4-isopropyl-1,3-thiazolidine. The thiazolidine was reacted with cyclopentyl bromide according to Method D2a to afford (4S)-2-(2-methyl-4-nitrophenylimino)-4-isopropyl-3-cyclopentyl-1,3-thiazolidine.

Sources & evidence

ORD record: ord-8e3bbff1cfb14735b2fe03e17f2fd2f1
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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