Hydrochloric Acid → HCID 16734139, compound

HRID 600215Notes

Reaction equation

HRID 600215 reaction equation
N[C:2]1[CH:3]=[C:4](C=CC=1)[CH2:5][N:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:9][S:8][C:7]1=[O:19].C([N:26]([CH:29]([CH3:31])[CH3:30])[CH2:27]C)(C)C.[CH2:32]([N:34]([CH2:39][CH3:40])[CH2:35][CH2:36][CH2:37][OH:38])[CH3:33].Cl.[OH-:42].[Na+]>C1COCC1.ClCCl>[CH2:32]([N:34]([CH2:39][CH3:40])[CH2:35][CH2:36][CH2:37][O:38][C:27](=[O:42])[NH:26][C:29]1[CH:30]=[CH:2][CH:3]=[C:4]([CH2:5][N:6]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[CH2:9][S:8][C:7]2=[O:19])[CH:31]=1)[CH3:33]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 121593-(Diethylamino)-1-propanolHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 57680503HCID 57680503, compound

Product 1

HCID 16734139HCID 16734139, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

199 mg (0.6 mmol) of 3-(3-aminobenzyl)-5-(4-chlorophenyl)-3,6-dihydro-1,3,4-thiadiazin-2-one are dissolved in 4 ml of THF in an 8 ml multi-stirrer vessel, 107 μl of diisopropylethylamine are added, the mixture is cooled in an ice/water bath, 78 μl of isopropylidene chloroformate are added dropwise, and the mixture is subsequently stirred at 70° C. for 1 h. The mixture is subsequently cooled to room temperature, and 107 μl (0.72 mmol) of 3-diethylaminopropan-1-ol is added, and the mixture is refluxed for 96 h. For work-up, the reaction mixture is diluted with 30 ml of dichloromethane, shaken with 20 ml of 1 N HCl and 20 ml of 2 N NaOH, dried over sodium sulfate, evaporated to dryness and purified by chromatography (dichloromethane/methanol: 9:1). The combined fractions containing the product are evaporated to dryness and crystallised from diethyl ether/petroleum ether 40-60, giving 128 mg of 3-diethylaminopropyl {3-[5-(4-chlorophenyl)-3,6-dihydro-2-oxo-6H-1,3,4-thiadiazin-3-ylmethyl]phenyl}carbamate (“A1”), m.p. 115-117°;

Workup

  1. temperaturethe mixture is cooled in an ice/water bath
  2. temperatureThe mixture is subsequently cooled to room temperature
  3. temperaturethe mixture is refluxed for 96 h
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. custompurified by chromatography (dichloromethane/methanol: 9:1)
  7. additionThe combined fractions containing the product
  8. customare evaporated to dryness
  9. customcrystallised from diethyl ether/petroleum ether 40-60

Sources & evidence

ORD record
ord-02e0e0914655434ebfcdcd9ffbed6b39
Source dataset
uspto-grants-2011_03
Patent number
US07902186B2

Reaction notes

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