Ethanol → 11-Morpholinodibenzo[b,f][1,4]thiazepin-3-carboxylic Acid 5,5-Dioxide

HRID 444153Notes

Reaction equation

HRID 444153 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:13]3[CH:14]=[CH:15][C:16]([C:18]([O:20]C)=[O:19])=[CH:17][C:12]=3[S:11](=[O:23])(=[O:22])[C:10]3[CH:24]=[CH:25][CH:26]=[CH:27][C:9]=3[N:8]=2)[CH2:3][CH2:2]1.[OH-].[K+].O.C(O)C>O1CCOCC1>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:13]3[CH:14]=[CH:15][C:16]([C:18]([OH:20])=[O:19])=[CH:17][C:12]=3[S:11](=[O:23])(=[O:22])[C:10]3[CH:24]=[CH:25][CH:26]=[CH:27][C:9]=3[N:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14797Potassium HydroxideHCID 13013938HCID 13013938, compound

Product 1

HCID 1301393711-Morpholinodibenzo[b,f][1,4]thiazepin-3-carboxylic Acid 5,5-Dioxide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Stir 386 mg (1 mmole) of the ester of Example 19 in a solution of 131.8 mg (2 mmole) of 85% aqueous potassium hydroxide, 1.3 ml of water, 6.5 ml of ethanol and 0.65 ml of dioxane at room temperature under argon for 1 hour. Evaporate to dryness and dissolve the residue in 5 ml of water. Acidify with acetic acid, separate the precipitate by filtration, wash with water and dry. Recrystallize from methanol to obtain the title product (m.p. 200-295 dec).

Workup

  1. customEvaporate to dryness
  2. dissolutiondissolve the residue in 5 ml of water
  3. customseparate the precipitate
  4. filtrationby filtration
  5. washwash with water
  6. customdry
  7. customRecrystallize from methanol

Sources & evidence

ORD record
ord-af7901b5ab03428d8d7344e3ab4738cb
Source dataset
uspto-grants-1981_04
Patent number
US04263207

Reaction notes

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