Thionyl Chloride → HCID 178428752, compound

HRID 276282Notes

Reaction equation

HRID 276282 reaction equation
C(OC([NH:8][C@@H:9]([CH:13]([CH3:15])[CH3:14])[CH2:10][CH2:11]O)=O)(C)(C)C.O=S(Cl)Cl.[CH3:20][C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:22]=1[N:30]=[C:31]=[S:32]>>[CH:13]([C@H:9]1[CH2:10][CH2:11][S:32][C:31](=[N:30][C:22]2[CH:23]=[CH:24][C:25]([N+:27]([O-:29])=[O:28])=[CH:26][C:21]=2[CH3:20])[NH:8]1)([CH3:15])[CH3:14]

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 1456212-Methyl-4-nitrophenyl isothiocyanateHCID 11715497Carbamic acid, [(1R)-1-(2-hydroxyethyl)-2-methylpropyl]-, 1,1-dimethylethyl

Product 1

HCID 178428752HCID 178428752, compoundYield 100%

Procedure

(R)-3-(tert-Butoxycarbonylamino)-4-methylpentanol (Method B6a) was reacted with SOCl2 followed by 2-methyl-4-nitrophenyl isothiocyanate in a manner analogous to Method C2a to afford (R)-4-isopropyl-2-(2-methyl-4-nitrophenylimino)-2,3,4,5-tetrahydro-1,3-thiazine (100%).

Sources & evidence

ORD record
ord-c5ca7604390042c8929a220f72899693
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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