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

HRID 597749Notes

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.CC[C:18](Cl)=[S:19].[CH3:21]CCCC(Cl)=S.CCCC(Cl)=S>>[CH3:21][S:19][CH2:18][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

Reactant 4

HCID 198068534-Methylthiobutyryl chloride

HCID 21249692Methylthioacetyl chloride

HCID 22343826Butanecarbothioyl chloride

HCID 737936803-(methylthio)-1-nitro-1-(tetrahydro-2H-1,3-thiazin-2-ylidene)-2-propanone

Product 1

HCID 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-2He1,3-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-8c4fa2f274e64cd3a9d27db137d760fc
Source dataset: uspto-grants-1977_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04015001

Reaction notes

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