Ammonium Chloride → HCID 178441410, compound

HRID 1602508Notes

Reaction equation

HRID 1602508 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([CH2:10][O:11][C:12]2[CH:13]=[C:14]([CH:41]=[CH:42][CH:43]=2)[C:15]([NH:17][C:18]2[CH:23]=[C:22]([CH2:24][CH2:25][CH2:26][S:27]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[CH:21]=[CH:20][C:19]=2[O:37][CH2:38][C:39]#[N:40])=[O:16])[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+].[N-:46]=[N+:47]=[N-:48].[Na+].S([O-])(O)(=O)=O.[Na+]>CN(C)C=O>[C:1]([C:5]1[N:6]=[C:7]([CH2:10][O:11][C:12]2[CH:13]=[C:14]([CH:41]=[CH:42][CH:43]=2)[C:15]([NH:17][C:18]2[CH:23]=[C:22]([CH2:24][CH2:25][CH2:26][S:27]([C:30]3[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=3)(=[O:28])=[O:29])[CH:21]=[CH:20][C:19]=2[O:37][CH2:38][C:39]2[NH:48][N:47]=[N:46][N:40]=2)=[O:16])[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 516919Sodium BisulfateHCID 19611382HCID 19611382, compound

Product 1

HCID 178441410HCID 178441410, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Dimethylformamide (13 ml) was added to a mixture of 3-[(4-tert-butyl-2-thiazolyl)methoxy]-5'-[3-(4-chlorophenylsulfonyl)propyl]-2'-cyanomethoxybenzanilide (1.30 g, 2.04 mmol), ammonium chloride (0.20 g, 4.08 mmol) and sodium azide (0.25 g, 4.08 mmol), and the resulting mixture was stirred at 70° C. for 12 hours. Ice and 5% sodium hydrogensulfate aqueous solution were added to the reaction solution and the product formed was extracted with ethyl acetate. The resulting organic layer was washed with water and brine in that order, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. Thereafter, the resulting residue was purified by silica gel column chromatography (eluent=methanol:chloroform=5:100) and then crystallized from acetonitrile to give 3-[(4-tert-butyl-2-thiazolyl)methoxy]-5'-[3-(4-chlorophenylsulfonyl)propyl]-2'-(1H-tetrazol-5-ylmethoxy)benzanilide (1.02 g, 74%) as colorless crystals.

Workup

  1. customthe product formed
  2. extractionwas extracted with ethyl acetate
  3. washThe resulting organic layer was washed with water and brine in that order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThereafter, the resulting residue was purified by silica gel column chromatography (eluent=methanol:chloroform=5:100)
  7. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-2f4aee6251694bf883014b827b5c5560
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Reaction notes

Loading…