Sodium Azide → HCID 91287135, compound

HRID 18642Notes

Reaction equation

HRID 18642 reaction equation
N([O-])=O.[Na+].[CH2:5]([O:7][C:8]([C:10]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[N:12]([C:22]2[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=2)[C:11]=1[CH3:29])=[O:9])[CH3:6].[N-:30]=[N+:31]=[N-].[Na+]>O.Cl>[CH2:5]([O:7][C:8]([C:10]1[CH:14]=[C:13]([C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[N:12]([C:22]2[CH:23]=[CH:24][C:25]([N:28]=[N+:30]=[N-:31])=[CH:26][CH:27]=2)[C:11]=1[CH3:29])=[O:9])[CH3:6]

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 14339168Ethyl 1-(4-aminophenyl)-5-(4-chlorophenyl)-2-methyl-1H-pyrrole-3-carboxylateHCID 23668193Sodium Nitrite

Product 1

HCID 91287135HCID 91287135, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of NaNO2 (0.015 g, 0.216 mmol) in water (1.5 mL) was added to an ice-cold solution of Example 26 (0.075 g, 0.212 mmol) in HCl (3 mL, 37% w/v) over 10 minutes. A solution of NaN3 (0.138 g, 2.12 mmol) in water (0.5 mL) was added drop wise with stirring at 0° C. over 10 minutes, and the temperature of the mixture was allowed to rise to 25° C. After stirring for another 20 minutes at room temperature, the mixture was extracted with DCM (3×25 mL), and the combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure to provide the titled compound. MS (ESI) m/z 381 (M+H); IR: 2097 cm−1.

Workup

  1. customto rise to 25° C
  2. stirringAfter stirring for another 20 minutes at room temperature
  3. extractionthe mixture was extracted with DCM (3×25 mL)
  4. dry with materialthe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b3df420185a24a37b29e5093aa921898
Source dataset
uspto-grants-2010_06
Patent number
US07741364B2

Reaction notes

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