Sodium Hydroxide → HCID 67756616, compound

HRID 981918Notes

Reaction equation

HRID 981918 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:11][N:12]1[C:18]2=[C:19]3[C:24](=[N:25][C:26]4[CH2:27][CH2:28][CH2:29][CH:16]([C:17]=42)[S:15][CH2:14][C:13]1=O)[CH:23]=[CH:22][CH:21]=[CH:20]3.[OH-].[Na+].[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37]>O1CCCC1>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37].[CH3:11][N:12]1[C:18]2=[C:19]3[C:24](=[N:25][C:26]4[CH2:27][CH2:28][CH2:29][CH:16]([C:17]=42)[S:15][CH2:14][CH2:13]1)[CH:23]=[CH:22][CH:21]=[CH:20]3

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 444266Maleic AcidHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 54329643HCID 54329643, compound

Product 1

HCID 67756616HCID 67756616, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 1M lithium aluminum hydride in tetrahydrofuran (14.1 ml), diluted with tetrahydrofuran (50 ml) was added aluminum chloride (1.9 g), followed by 1,3,4a,5,6,7-hexahydro-1-methyl-2H-quino-[4,3,2-ef][1,4]benzthiazepin-2-one (3.42 g). After stirring for 1 hr, the reaction mixture was poured into iced sodium hydroxide solution and extracted three times with ethyl acetate. The combined organic extracts were washed with water, saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was dissolved in methanol and treated with maleic acid (1.1 eq). Crystallization with ethyl ether followed by recrystallization from methanol/ethyl ether gave 3.17 g (73.0%) of product, mp 200°-201° C. (dec).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic extracts were washed with water, saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in methanol
  7. customCrystallization with ethyl ether
  8. customfollowed by recrystallization from methanol/ethyl ether

Sources & evidence

ORD record
ord-bf3225bf93e74453a717e9826137ade6
Source dataset
uspto-grants-1991_02
Patent number
US04994452

Reaction notes

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