Dimethylformamide → HCID 178427455, compound

HRID 1417323Notes

Reaction equation

HRID 1417323 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N-:25]=[N+:26]=[N-:27].[Na+].[Cl-].[NH4+].CN(C)C=O>C(O)(=O)C.O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[NH:27][N:26]=[N:25][N:24]=3)=[CH:21][CH:22]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 67599375HCID 67599375, compound

Product 1

HCID 178427455HCID 178427455, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 3.4 g of 4-methyl-N-[4-(4-cyanophenoxy)butyl]benzenesulfonamlde (Example 53), 1.3 g of sodium azide, 1.5 g of ammonium chloride, and 25 ml of dimethylformamide is stirred at 120°-130° C. (oil bath) for 16 hours. The reaction mixture is added to 200 ml of water and the resultant solution then acidified to pH 4-5 with acetic acid. The precipitate that forms is collected, washed with water, dried and recrystallized from boiling ethanol. Cooling gives the pure compound, m.p. 180°-182° C.; yield, 2.4 g.

Workup

  1. customThe precipitate that forms is collected
  2. washwashed with water
  3. customdried
  4. customrecrystallized
  5. temperatureCooling
  6. customgives the pure compound, m.p. 180°-182° C.
  7. customyield

Sources & evidence

ORD record
ord-a5a3dedc28ed4b92b860780953a5f093
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Reaction notes

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