Water → HCID 19711091, compound

HRID 724811Notes

Reaction equation

HRID 724811 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:10])[CH3:9].[CH2:12]([N:14]([CH2:17][CH2:18][O:19][C:20]([N:22]1[N:27]=[C:26]([C:28]2[CH:29]=[C:30]3[C:35](=[CH:36][CH:37]=2)[NH:34][CH2:33][CH2:32][CH2:31]3)[CH:25]([CH3:38])[S:24][C:23]1=[O:39])=[O:21])[CH2:15][CH3:16])[CH3:13].O>ClCCl>[CH2:12]([N:14]([CH2:17][CH2:18][O:19][C:20]([N:22]1[N:27]=[C:26]([C:28]2[CH:29]=[C:30]3[C:35](=[CH:36][CH:37]=2)[N:34]([C:8](=[O:10])[CH3:9])[CH2:33][CH2:32][CH2:31]3)[CH:25]([CH3:38])[S:24][C:23]1=[O:39])=[O:21])[CH2:15][CH3:16])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 19711063HCID 19711063, compound

Product 1

HCID 19711091HCID 19711091, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

5 ml of triethylamine and then, dropwise with stirring, 4 ml of acetyl chloride are added to a solution of 12 g of 3-[2-(N,N-diethylamino)ethoxycarbonyl]-5-(1,2,3,4-tetrahydro-6-quinolyl)-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one [obtainable in analogy to Example 1 by reacting 5-(1,2,3,4-tetrahydro-6-quinolyl)-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one with 2-(N,N-diethylamino)ethyl chloroformate] in 100 ml of dichloromethane. The mixture is subsequently stirred at 20° C. for one hour and decomposed with water and the mixture is worked up in the conventional manner to give 3-[2-(N,N-diethylamino)ethoxycarbonyl]-5-(1-acetyl-1,2,3,4-tetrahydro-6-quinolyl)-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one.

Sources & evidence

ORD record
ord-4c2148e9d3db4aec86771b9d80b1b97c
Source dataset
uspto-grants-1998_01
Patent number
US05705497

Reaction notes

Loading…