Ammonium Chloride → HCID 14126425, compound

HRID 568574Notes

Reaction equation

HRID 568574 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=O)[C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[S:7][C:6]=2[CH:17]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+].C(=O)(O)[O-].[Na+]>O1CCCC1.C(N1CCOCC1)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[S:7][C:6]=2[CH:17]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 14126422HCID 14126422, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14126425HCID 14126425, compound

Reagents, catalysts & solvents 2

HCID 7525EthylmorpholineSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 10,11-dihydro-7-hydroxy-11-oxodibenzo[b,f][1,4]thiazepin (4.5g,18.5 mmoles) and lithium aluminum hydride (3.5g,92.5 mmoles) in tetrahydrofuran (200 ml) and N-ethylmorpholine (100 ml) was refluxed for 18 hours. The reaction mixture was decomposed by the addition of 12 ml of a saturated solution of ammonium chloride and 33 ml of lM sodium bicarbonate. The mixture was filtered and the salts were washed with methanol. The filtrate was evaporated to dryness and the residue was extracted several times with ether. Chromatography of the residue on silica gel, eluting with 5% methanol in chloroform, afforded the title compound, m.p. 172°-174°.

Workup

  1. temperaturewas refluxed for 18 hours
  2. filtrationThe mixture was filtered
  3. washthe salts were washed with methanol
  4. customThe filtrate was evaporated to dryness
  5. extractionthe residue was extracted several times with ether
  6. washChromatography of the residue on silica gel, eluting with 5% methanol in chloroform

Sources & evidence

ORD record
ord-c42c898ba63a4c33a36d955fa86c0f6c
Source dataset
uspto-grants-1988_03
Patent number
US04728735

Reaction notes

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