Triethylamine → 3-[(-)-camphanoyl]-5-[1-(3,4-methylenedioxybenzoyl)-1,2,3, 4-tetrahydroquinol-6-yl]-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one

HRID 1591249Notes

Reaction equation

HRID 1591249 reaction equation
[C:1]12([CH3:13])[C:7]([CH3:9])([CH3:8])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[C:10](Cl)=[O:11].[CH2:14]1[O:42][C:41]2[CH:40]=[CH:39][C:18]([C:19]([N:21]3[C:30]4[C:25](=[CH:26][C:27]([C:31]5[CH:36]([CH3:37])[S:35][C:34](=[O:38])[NH:33][N:32]=5)=[CH:28][CH:29]=4)[CH2:24][CH2:23][CH2:22]3)=[O:20])=[CH:17][C:16]=2[O:15]1.C(N(CC)CC)C>C(Cl)Cl>[C:1]12([CH3:13])[C:7]([CH3:9])([CH3:8])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[C:10]([N:33]1[N:32]=[C:31]([C:27]2[CH:26]=[C:25]3[C:30](=[CH:29][CH:28]=2)[N:21]([C:19](=[O:20])[C:18]2[CH:39]=[CH:40][C:41]4[O:42][CH2:14][O:15][C:16]=4[CH:17]=2)[CH2:22][CH2:23][CH2:24]3)[CH:36]([CH3:37])[S:35][C:34]1=[O:38])=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 118257245-[1-(3,4-methylenedioxybenzoyl)-1,2,3, 4-tetrahydroquinol-6-yl]-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-oneHCID 534427834,7,7-Trimethyl-3-bicyclo[2.2.1]heptanecarbonyl chloride

Product 1

HCID 678849993-[(-)-camphanoyl]-5-[1-(3,4-methylenedioxybenzoyl)-1,2,3, 4-tetrahydroquinol-6-yl]-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 26 g of (-)-camphanic acid chloride in 100 ml of methylene chloride is added dropwise at 0°, with stirring, to a suspension of 48 g of 5-[1- (3,4-methylenedioxybenzoyl)-1,2,3, 4-tetrahydroquinol-6- yl]-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one in 800 ml of methylene chloride to which 20 ml of triethylamine have been added, and the reaction mixture is stirred for 4 hours. It is then washed with dilute hydrochloric acid and subsequently with bicarbonate solution. The organic phase is separated off and worked up in conventional manner to give 3-[(-)-camphanoyl]-5-[1-(3,4-methylenedioxybenzoyl)-1,2,3, 4- tetrahydroquinol-6-yl]-6-methyl-3,6-dihydro-2H-1,3,4- thiadiazin-2-one as a mixture of diastereoisomers, m.p. 216°-217° .

Workup

  1. additionhave been added
  2. washIt is then washed with dilute hydrochloric acid and subsequently with bicarbonate solution
  3. customThe organic phase is separated off

Sources & evidence

ORD record
ord-a19d865a2478427c977140d5abb19f6d
Source dataset
uspto-grants-1993_04
Patent number
US05206363

Reaction notes

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