Ammonium Chloride → HCID 178428377, compound

HRID 2305969Notes

Reaction equation

HRID 2305969 reaction equation
[CH:1]1([CH2:4][S:5]([C:8]2[CH:9]=[C:10]([CH:23]=[CH:24][C:25]=2[OH:26])[O:11][C:12]2[C:17]([CH3:18])=[CH:16][C:15]([NH:19][C:20]#[N:21])=[CH:14][C:13]=2[CH3:22])(=[O:7])=[O:6])[CH2:3][CH2:2]1.[N-:27]=[N+:28]=[N-:29].[Na+].[Cl-].[NH4+]>>[CH:1]1([CH2:4][S:5]([C:8]2[CH:9]=[C:10]([O:11][C:12]3[C:17]([CH3:18])=[CH:16][C:15]([NH:19][C:20]4[NH:29][N:28]=[N:27][N:21]=4)=[CH:14][C:13]=3[CH3:22])[CH:23]=[CH:24][C:25]=2[OH:26])(=[O:7])=[O:6])[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 86584201HCID 86584201, compound

Product 1

HCID 178428377HCID 178428377, compound

Conditions

Temperature
140 °C

Procedure

2-Cyclopropylmethanesulfonyl-4-[2,6-dimethyl-4-(1H-tetrazol-5-ylamino)-phenoxy]-phenol was prepared from 4-(3-cyclopropylmethanesulfonyl-4-hydroxy-phenoxy)-3,5-dimethyl-phenyl-cyanamide according to a procedure analogous to that described in EXAMPLE 1, Step C. Sodium azide (1.5 equiv) and ammonium chloride (10 equiv) were used, and the reaction was heated to 140° C. for 20 hours. After the reaction had been acidified, the aqueous mixture was extracted with ethyl acetate (3×10 ml). The combined organic extracts were washed with aqueous 1N HCl (3×50 ml), and brine (50 ml). The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by preparative TLC (methanol:water:dichloromethane=15:1.5:83.5) to afford the title product of Example 7. MS (APCI−) Calc.: 415.1, Found: 413.8 (M−1).

Workup

  1. extractionthe aqueous mixture was extracted with ethyl acetate (3×10 ml)
  2. washThe combined organic extracts were washed with aqueous 1N HCl (3×50 ml), and brine (50 ml)
  3. dry with materialThe organic phase was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC (methanol:water:dichloromethane=15:1.5:83.5)

Sources & evidence

ORD record
ord-49db1122dbd647dc9a2858ffede68656
Source dataset
uspto-grants-2002_08
Patent number
US06441015B2

Reaction notes

Loading…