Sodium Chloride → HCID 20559336, compound

HRID 1659525Notes

Reaction equation

HRID 1659525 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]3[CH2:16][CH2:17][CH:11]([CH2:12][CH:13]3[C:18](O)=[O:19])[C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].ClC(OCC)=O.[N-:27]=[N+:28]=[N-:29].[Na+].[Cl-].[Na+]>O1CCCC1.O.C(N(CC)CC)C>[CH2:1]([N:3]1[C:15]2[CH:14]3[CH2:16][CH2:17][CH:11]([CH2:12][CH:13]3[C:18]([N:27]=[N+:28]=[N-:29])=[O:19])[C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 12798061HCID 12798061, compound

Product 1

HCID 20559336HCID 20559336, compoundYield 91.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 9-ethyl-1,2,3,4-tetrahydro-1,4-ethanocarbazole-2-carboxylic acid (5.0 g, 0.0186 mole, described in Example 3) in dry tetrahydrofuran (50 ml), under nitrogen at 20°-22° C., triethylamine (11.5 ml) was added, followed by ethyl chloroformate (2.8 ml) at 20° C. After stirring at room temperature for 3 hr, the suspension of mixed anhydride was cooled to -10° C. and treated dropwise with a solution of sodium azide (2.94 g in 10 ml of water). The slurries were stirred for 1 hr at -10° C. Water was added and saturated with sodium chloride, then extracted with diethyl ether. The organic layer was washed with water, dried, evaporated to give a yellow oil (ca. 5 g) of 9-ethyl-2,3,4,9-tetrahydro-1,4-ethano-1H-carbazole-2-carbonyl azide: IR (CHCl3) 2135 cm-1.

Workup

  1. temperaturewas cooled to -10° C.
  2. stirringThe slurries were stirred for 1 hr at -10° C
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-1da1e9701a154c7793ff18b14bf49a14
Source dataset
uspto-grants-1981_12
Patent number
US04304772

Reaction notes

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