2-Methyl-4-nitrophenyl isothiocyanate → HCID 178428755, compound

HRID 276478Notes

Reaction equation

HRID 276478 reaction equation
[CH:1]([C@H:4]([NH2:7])[CH2:5]O)([CH3:3])[CH3:2].[Cl-].ClC[C@@H]([NH3+])C(C)C.[CH3:16][C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1[N:26]=[C:27]=[S:28]>>[CH3:16][C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1[N:26]=[C:27]1[NH:7][C@@H:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][S:28]1

Participants

4

Reactant 3

HCID 1456212-Methyl-4-nitrophenyl isothiocyanateHCID 640993L-ValinolHCID 86590173HCID 86590173, compound2×

Product 1

HCID 178428755HCID 178428755, compound

Procedure

(1S)-1-Isopropyl-2-hydroxyethylamine was converted to (1S)-2-chloro-1-isopropylethylammonium chloride according to Method B7a. 2-Methyl-4-nitrophenyl isothiocyanate was reacted with (1S)-2-chloro-1-isopropylethylammonium chloride according to Method C1a to give (45)-2-(2-methyl-4-nitrophenylimino)-4-isopropyl-1,3-thiazolidine. The thiazolidine was reacted with isobutyl bromide according to Method D2a to afford (4S)-2-(2-methyl -4-nitrophenylimino)-4-isopropyl-3-isobutyl-1,3-thiazolidine HCl salt.

Sources & evidence

ORD record
ord-57d7b3c2bb2c4e53b0f574f60b8ff6f1
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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