Ammonium Chloride → HCID 178428378, compound

HRID 2305963Notes

Reaction equation

HRID 2305963 reaction equation
[Cl:1][C:2]1[CH:22]=[C:21]([NH:23][C:24]#[N:25])[CH:20]=[C:19]([CH3:26])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([OH:18])=[C:9]([S:11]([NH:14][CH:15]2[CH2:17][CH2:16]2)(=[O:13])=[O:12])[CH:10]=1.[N-:27]=[N+:28]=[N-:29].[Na+].[Cl-].[NH4+]>>[Cl:1][C:2]1[CH:22]=[C:21]([NH:23][C:24]2[NH:29][N:28]=[N:27][N:25]=2)[CH:20]=[C:19]([CH3:26])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([OH:18])=[C:9]([S:11]([NH:14][CH:15]2[CH2:16][CH2:17]2)(=[O:12])=[O:13])[CH:10]=1

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 18433414HCID 18433414, compound

Product 1

HCID 178428378HCID 178428378, compound

Conditions

Temperature
165 °C

Procedure

5-[2-Chloro-6-methyl-4-(1H-tetrazol-5-ylamino)-phenoxy]-N-cyclopropyl-2-hydroxy-benzenesulfon-amide was prepared from 5-[2-chloro-4-cyanoamino-6-methyl-phenoxy]-N-cyclopropyl-2-hydroxy-benzenesulfonamide according to a procedure analogous to that described in EXAMPLE 1, Step C. Sodium azide (1.2 equiv) and ammonium chloride (10 equiv) were used, and the reaction was heated to 165° C. for 3 hours. After the reaction had been acidified, the aqueous mixture was washed with ethyl acetate (3×10 ml). The combined organic extracts were extracted 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 25:3:72) to afford the title product of Example 5. MS (APCI+) Calc.: 436.1, Found: 436.9 (M+1).

Workup

  1. washthe aqueous mixture was washed with ethyl acetate (3×10 ml)
  2. extractionThe combined organic extracts were extracted 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 25:3:72)

Sources & evidence

ORD record
ord-56131e2268e947f987c6a60bea00b67e
Source dataset
uspto-grants-2002_08
Patent number
US06441015B2

Reaction notes

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