1,4-Tetrahydrothiazine-3-one → 4-Benzylthiomorpholin-3-one

HRID 2230090Notes

Reaction equation

HRID 2230090 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1Cl)[CH2:5][N:6]1[CH2:11][CH2:10][S:9][CH2:8][C:7]1=[O:12].ClC1C=C(C=CC=1Cl)CBr.N1CCSCC1=O>>[CH2:5]([N:6]1[CH2:11][CH2:10][S:9][CH2:8][C:7]1=[O:12])[C:4]1[CH:3]=[CH:2][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 884021,4-Tetrahydrothiazine-3-oneHCID 6397264-(Bromomethyl)-1,2-dichlorobenzeneHCID 120830114-(3,4-Dichlorobenzyl)-thiomorpholin-3-one

Product 1

HCID 149411724-Benzylthiomorpholin-3-one

Procedure

In the same manner, 4-(3,4-dichlorobenzyl)-thiomorpholin-3-one was prepared in 89% yield from 3,4-dichlorobenzyl bromide and thiomorpholin-3-one as a white solid. M.p. 86-87° C. 1H-NMR (CDCl3, 400 MHz) d 7.38 (1H, d), 7.33 (1H, d), 7.10 (1H, dd), 4.56 (2H, s), 3.55-3.51 (2H, m), 3.37 (2H, s), 2.81-2.76 (2H, m).

Sources & evidence

ORD record
ord-d4f4952896e34588bf5186e45e5bbe1c
Source dataset
uspto-grants-2002_07
Patent number
US06423708B1

Reaction notes

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