4-Methylthiobutyryl chloride → 5-(methylthio)-1-nitro-1-(tetrahydro-2H-1,3-thiazin-2-ylidene)-2-pentanone

HRID 1657700Notes

Reaction equation

HRID 1657700 reaction equation
CS[CH2:3][C:4](=[O:15])[C:5]([N+:12]([O-:14])=[O:13])=[C:6]1[NH:11][CH2:10][CH2:9][CH2:8][S:7]1.[CH3:16][CH2:17][C:18](Cl)=[S:19].[CH3:21]CCC[C:25](Cl)=[S:26].CCCC(Cl)=S>>[CH3:21][S:19][CH2:18][CH2:17][CH2:3][C:4](=[O:15])[C:5]([N+:12]([O-:14])=[O:13])=[C:6]1[NH:11][CH2:10][CH2:9][CH2:8][S:7]1.[CH3:16][S:26][CH2:25][CH2:3][C:4](=[O:15])[C:5]([N+:12]([O-:14])=[O:13])=[C:6]1[NH:11][CH2:10][CH2:9][CH2:8][S:7]1

Participants

6

Reactant 4

HCID 198068534-Methylthiobutyryl chlorideHCID 21249692Methylthioacetyl chlorideHCID 22343826Butanecarbothioyl chlorideHCID 737936803-(methylthio)-1-nitro-1-(tetrahydro-2H-1,3-thiazin-2-ylidene)-2-propanone

Product 2

HCID 737936815-(methylthio)-1-nitro-1-(tetrahydro-2H-1,3-thiazin-2-ylidene)-2-pentanoneHCID 737936824-(methylthio)-1-nitro-1-(tetrahydro-2H-1,3-thiazin-2-ylidene)-2-butanone

Procedure

In a similar manner, 3-(methylthio)-1-nitro-1-(tetrahydro-2H-1,3-thiazin-2-ylidene)-2-propanone (18) was prepared as a yellow solid, m.p.: 117.5°-119°, from methylthioacetyl chloride; 5-(methylthio)-1-nitro-1-(tetrahydro-2H-1,3-thiazin-2-ylidene)-2-pentanone (19) was prepared as a pale yellow solid, m.p.: 49°-49.5°, from 4-methylthiobutyryl chloride; 4-(methylthio)-1-nitro-1-(tetrahydro-2H-1,3-thiazin-2-ylidene)-2-butanone (20) was prepared as a yellow solid, m.p.: 42°-43° from 3-methylthiopropionyl chloride.

Sources & evidence

ORD record
ord-ddbb82babc394e79ab56a55855082fee
Source dataset
uspto-grants-1976_06
Patent number
US03962225

Reaction notes

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