Sodium Chloride → HCID 13021078, compound

HRID 1446811Notes

Reaction equation

HRID 1446811 reaction equation
[NH2:1]OS(=O)=O.[H-].[Na+].[C:8]1(=[O:19])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11][CH2:10][NH:9]1.[Na+].[Cl-]>CN(C)C=O.O1CCCC1>[NH2:1][N:9]1[CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:8]1=[O:19]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 112406552,3,4,5-Tetrahydro-benzo[c]azepin-1-oneHCID 178514657HCID 178514657, compound

Product 1

HCID 13021078HCID 13021078, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.7 g of O-amino-sulfonic acid and 1.25 g of a 55% oily suspension of sodium hydride in 30 ml of dimethylformamide and 30 ml of tetrahydrofuran was gradually added at a temperature of 10° C. to a suspension of 9.66 g (0.0176 mol) 4,5-dihydro-2-benzazepine-1(2H,3H)-one. After standing for 1 hour at room temperature the mixture was poured into a saturated aqueous solution of NaCl, then the organic layer was separated and the mother liquors were extracted with 300 ml (3×100 ml) of an 1:1 (v:v) mixture of tetrahydrofuran and dimethylformamide. The organic phases were combined and brought to dryness. The obtained residue was subsequently taken up with 500 ml of ethyl acetate and the resulting organic solution was extracted with 200 ml (5×40 ml) of a 3% aqueous solution of HCl. The acidic extract was made alkaline with 5% aqueous sodium hydroxide and subsequently extracted with ethyl acetate. After evaporating the solvent, an oily residue was obtained which was distilled under reduced pressure. Yield: 10 g. of the title compound. B.p. 120° C./0.2 mmHg

Workup

  1. customthe organic layer was separated
  2. extractionthe mother liquors were extracted with 300 ml (3×100 ml) of an 1:1 (v:v) mixture of tetrahydrofuran and dimethylformamide
  3. extractionthe resulting organic solution was extracted with 200 ml (5×40 ml) of a 3% aqueous solution of HCl
  4. extractionThe acidic extract
  5. extractionsubsequently extracted with ethyl acetate
  6. customAfter evaporating the solvent
  7. customan oily residue was obtained which
  8. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-c715101eedd6491686439bafe3129280
Source dataset
uspto-grants-1982_02
Patent number
US04313950

Reaction notes

Loading…