Citric Acid → HCID 178441409, compound

HRID 1602502Notes

Reaction equation

HRID 1602502 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([CH2:10][CH2:11][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+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[C:1]([C:5]1[N:6]=[C:7]([CH2:10][CH2:11][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:29])=[O:28])[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 311Citric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 19611387HCID 19611387, compound

Product 1

HCID 178441409HCID 178441409, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Dimethylformamide (5.0 ml) was added to a mixture of 3-[2-(4-tert-butyl-2-thiazolyl)ethyl]-5'-[3-(4-chlorophenylsulfonyl)propyl]-2'-cyanomethoxybenzanilide (0.57 g, 0.90 mmol), ammonium chloride (96 mg, 1.8 mmol) and sodium azide (0.12 g, 1.9 mmol), and the resulting mixture was stirred at 70° C. for 12 hours. Ice and 10% citric acid 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. The resulting residue was purified by silica gel column chromatography (eluent=methanol:chloroform=3:100) and then crystallized from acetonitrile to give 3-[2-(4-tert-butyl-2-thiazolyl)ethyl]-5'-[3-(4-chlorophenylsulfonyl)propyl]-2'-(1H-tetrazol-5-ylmethoxy)benzanilide (0.34 g, 0.50 mmol, 56%) as colorless crystals. Its structure is shown in Table 30.

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. customThe resulting residue was purified by silica gel column chromatography (eluent=methanol:chloroform=3:100)
  7. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-37861b21bea04762a47fa30d01bcaffb
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Reaction notes

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