Sodium Azide → HCID 470749, compound

HRID 724935Notes

Reaction equation

HRID 724935 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[CH:29]=[N:28][C:13]3[N:14]([CH2:26][CH3:27])[C:15]4[N:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:16]=4[N:17]([CH3:20])[C:18](=[O:19])[C:12]=3[CH:11]=2)[CH:5]=[CH:6][CH:7]=1.N([O-])=O.[Na+].[N-:34]=[N+:35]=[N-].[Na+]>Cl.O>[N:1]([C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[CH:29]=[N:28][C:13]3[N:14]([CH2:26][CH3:27])[C:15]4[N:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:16]=4[N:17]([CH3:20])[C:18](=[O:19])[C:12]=3[CH:11]=2)[CH:5]=[CH:6][CH:7]=1)=[N+:34]=[N-:35]

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 470757HCID 470757, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 470749HCID 470749, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

8-[2-(3-Aminophenyl)ethyl]-2-chloro-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.22 g, 0.54 mmol) was dissolved in 0.55 mL of concentrated hydrochloric acid. Water (2.8 mL) was added and the solution was cooled to 0° C. producing a precipitate. A solution of sodium nitrite (0.19 g, 2.75 mmol) in 8 mL of water was added dropwise. After 20 min, a solution of sodium azide (0.27 g, 4.15 mmol) in 3 mL of water was added in the dark. After 15 min, the product was extracted with ethyl acetate. Purification by flash chromatography, eluting with ethyl acetate/hexanes, and recrystallization (ether/petroleum ether) afforded 0.17 g of the title compound, m.p. 104°-105° C.

Workup

  1. customproducing a precipitate
  2. waitAfter 15 min
  3. extractionthe product was extracted with ethyl acetate
  4. customPurification by flash chromatography
  5. washeluting with ethyl acetate/hexanes, and recrystallization (ether/petroleum ether)

Sources & evidence

ORD record
ord-c36008d6a63f453ca0e54c6cb5d7af7f
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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