Isobutylamine → 5-[4-(isobutylamino)-3-nitrophenyl]-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one

HRID 1517180Notes

Reaction equation

HRID 1517180 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]([CH3:14])[S:12][C:11](=[O:15])[NH:10][N:9]=2)=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].[CH2:19]([NH2:23])[CH:20]([CH3:22])[CH3:21]>C(#N)C>[CH2:19]([NH:23][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]([CH3:14])[S:12][C:11](=[O:15])[NH:10][N:9]=2)=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17])[CH:20]([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 6558IsobutylamineHCID 148515165-(4-chloro-3-nitrophenyl)-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one

Product 1

HCID 595690275-[4-(isobutylamino)-3-nitrophenyl]-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-oneYield 80.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To 15 ml of acetonitrile are added 2.9 g (10.1 mM) of 5-(4-chloro-3-nitrophenyl)-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one and 5 ml (50 mM) of isobutylamine. The reaction medium is maintained at 60° C. for 20 hours with stirring and is then concentrated under vacuum. The residue obtained is purified on silica using dichloromethane as eluent. The product obtained is taken up and crystallised from diethyl ether. The solid is filtered off and washed to give 2.6 g of 5-[4-(isobutylamino)-3-nitrophenyl]-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one.

Workup

  1. concentrationis then concentrated under vacuum
  2. customThe residue obtained
  3. customis purified on silica
  4. customThe product obtained
  5. customcrystallised from diethyl ether
  6. filtrationThe solid is filtered off
  7. washwashed

Sources & evidence

ORD record
ord-86c9682da93942358b8cbb823ffad1e3
Source dataset
uspto-grants-2012_07
Patent number
US08232272B2

Reaction notes

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