Triethylamine → 2-Chloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylacetyl Azide

HRID 67641Notes

Reaction equation

HRID 67641 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[CH:6]([CH2:15][C:16](O)=[O:17])[C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1.C(N(CC)CC)C.ClC(OCC)=O.[N-:34]=[N+:35]=[N-:36].[Na+]>O1CCCC1.O.C(OCC)C>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[CH:6]([CH2:15][C:16]([N:34]=[N+:35]=[N-:36])=[O:17])[C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 205274972-Chloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylacetic Acid

Product 1

HCID 205274942-Chloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylacetyl Azide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

To a magnetically stirred, ice cold solution of 2-chloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylacetic acid (20.0 g, described in Example 2) in dry tetrahydrofuran (400 ml) is added, under an atmosphere of dry nitrogen, triethylamine (13 ml) and ethyl chloroformate (11.6 g). After stirring for 1 hr at 0° C., the suspension is cooled to -10° C. and a solution of sodium azide (6.4 g) in distilled water (40 ml) is added. After stirring for a further 1 hr at -10° C., the reaction mixture is diluted with diethyl ether (200 ml). The organic phase is dried over magnesium sulfate and evaporated to give the title compound.

Workup

  1. stirringAfter stirring for 1 hr at 0° C.
  2. stirringAfter stirring for a further 1 hr at -10° C.
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-8351b839dccc4aec8ac725de4ee6eb88
Source dataset
uspto-grants-1982_08
Patent number
US04346090

Reaction notes

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