Sodium Chloride → HCID 135583123, compound

HRID 1253010Notes

Reaction equation

HRID 1253010 reaction equation
[C:1]([C:6]1[CH:40]=[C:39]([C:41]([CH2:44][CH3:45])([CH3:43])[CH3:42])[CH:38]=[CH:37][C:7]=1[O:8][CH:9]([CH2:35][CH3:36])[C:10]([NH:12][C:13]1[CH:14]=[C:15]([CH:32]=[CH:33][CH:34]=1)[C:16]([NH:18][C:19]1[CH:20]=[CH:21][C:22]2[C:23]([C:30]=1[OH:31])=[CH:24][CH:25]=[CH:26][C:27](=[O:29])[N:28]=2)=[O:17])=[O:11])([CH2:4][CH3:5])([CH3:3])[CH3:2].S(Cl)([Cl:49])(=O)=O.C(OCC)(=O)C.[Cl-].[Na+]>C(Cl)Cl>[Cl:49][C:21]1[C:22]2[C:23](=[CH:24][CH:25]=[CH:26][C:27](=[O:29])[N:28]=2)[C:30]([OH:31])=[C:19]([NH:18][C:16](=[O:17])[C:15]2[CH:32]=[CH:33][CH:34]=[C:13]([NH:12][C:10](=[O:11])[CH:9]([O:8][C:7]3[CH:37]=[CH:38][C:39]([C:41]([CH2:44][CH3:45])([CH3:42])[CH3:43])=[CH:40][C:6]=3[C:1]([CH2:4][CH3:5])([CH3:3])[CH3:2])[CH2:35][CH3:36])[CH:14]=2)[CH:20]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 24648Sulfuryl chlorideHCID 135583125HCID 135583125, compound

Product 1

HCID 135583123HCID 135583123, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 30 ml of methylene chloride was dispersed 6 g of the 7-{3-[2-(2,4-di-t-amylphenoxy)butanoylamino]benzoylamino}-6-hydroxybenzazepin-2-one prepared in (6) above, and 0.84 ml of sulfuryl chloride was added drop-wise to the dispersion at room temperature. After stirring at room temperature for 2 hours, ethyl acetate and a saturated aqueous solution of sodium chloride were added thereto to effect extraction. The extract was concentrated under reduced pressure, and the residue was dispersed in 30 ml of acetonitrile and 15 ml of ethyl acetate. The dispersion was heat-refluxed, followed by cooling. The precipitated crystals were collected by filtration and dried to obtain 5.8 g of the desired coupler having a melting point of 234° to 236° C.

Workup

  1. additionwas added drop-wise to the dispersion at room temperature
  2. extractionextraction
  3. concentrationThe extract was concentrated under reduced pressure
  4. additionthe residue was dispersed in 30 ml of acetonitrile
  5. temperatureThe dispersion was heat-refluxed
  6. temperatureby cooling
  7. filtrationThe precipitated crystals were collected by filtration
  8. customdried
  9. customto obtain 5.8 g of the desired coupler

Sources & evidence

ORD record
ord-9e69dbbe85be4e8b80f90777c4548245
Source dataset
uspto-grants-1988_05
Patent number
US04746602

Reaction notes

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