2,6-Dimethyl-4-nitroaniline → HCID 178428753, compound

HRID 276449Notes

Reaction equation

HRID 276449 reaction equation
O[CH2:2][C@@H:3]([NH2:8])[CH2:4][CH:5]([CH3:7])[CH3:6].CC1C=C([N+]([O-])=O)C=C(C)C=1N.C[C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[C:24]([CH3:31])[C:23]=1[N:32]=[C:33]=[S:34]>>[CH3:31][C:24]1[CH:25]=[C:26]([N+:28]([O-:30])=[O:29])[CH:27]=[CH:22][C:23]=1[N:32]=[C:33]1[NH:8][C@@H:3]([CH2:4][CH:5]([CH3:7])[CH3:6])[CH2:2][S:34]1

Participants

4

Reactant 3

HCID 281592,6-Dimethyl-4-nitroanilineHCID 111307L-LeucinolHCID 124624312,6-Dimethyl-4-nitrophenyl isothiocyanate2×

Product 1

HCID 178428753HCID 178428753, compound

Procedure

(1S)-1-(Hydroxymethyl)-3-methylbutylamine was converted to (1S)-1-(chloromethyl)-3-methylbutanammonium chloride as described in Method B7a. 2,6-Dimethyl-4-nitroaniline was converted into 2,6-dimethyl-4-nitrophenyl isothiocyanate according to Method A2b. 2,6-Dimethyl-4-nitrophenyl isothiocyanate was reacted with (1S)-1-(chloromethyl)-3-methylbutanammonium chloride according to Method C1a to give (4S)-2-(2-methyl-4-nitrophenylimino)-4-isobutyl-1,3-thiazolidine. The thiazolidine was reacted with isobutyl bromide according to Method D2a to give (4S)-2-(2,6-dimethyl-4-nitrophenylimino)-3,4-diisobutyl-1,3-thiazolidine HCl salt.

Sources & evidence

ORD record
ord-c8f901655edd4a84821309d9759a0a3f
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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