Trifluoroacetyl chloride → 3-(4-Trifluoroacetamidobenzyl)-5-(3,4-dimethoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one

HRID 377167

Reaction equation

HRID 377167 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3](Cl)=[O:4].[NH2:8][C:9]1[CH:34]=[CH:33][C:12]([CH2:13][N:14]2[N:19]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=3)[CH:17]([CH2:30][CH3:31])[S:16][C:15]2=[O:32])=[CH:11][CH:10]=1>ClCCl.C(N(CC)CC)C>[F:1][C:2]([F:7])([F:6])[C:3]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]2[N:19]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=3)[CH:17]([CH2:30][CH3:31])[S:16][C:15]2=[O:32])=[CH:33][CH:34]=1)=[O:4]

Participants

5

Reactant 2

HCID 61106Trifluoroacetyl chlorideHCID 101346893-(4-Aminobenzyl)-5-(3,4-dimethoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one

Product 1

HCID 102061183-(4-Trifluoroacetamidobenzyl)-5-(3,4-dimethoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

0.8 ml of trifluoroacetyl chloride is added with stirring and ice cooling to a solution of 1.4 g of 3-(4-amino-benzyl)-5-(3,4-dimethoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one ("D") in 60 ml of dichloromethane and 1 ml of triethylamine, and the mixture is subsequently stirred for 3 hours. The solvent is removed and the residue is worked up in the conventional manner. Recrystallization from isopropanol/petroleum ether gives 1.9 g of 3-(4-trifluoroacetamidobenzyl)-5(3,4-dimethoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one, m.p. 124°.

Workup

  1. customThe solvent is removed
  2. customRecrystallization from isopropanol/petroleum ether

Sources & evidence

ORD record
ord-2a2f19add13044d39057729e18f2522f
Source dataset
uspto-grants-2000_02
Patent number
US06025354

Linked notes

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