Ethyl Acetate → HCID 178483180, compound

HRID 129684Notes

Reaction equation

HRID 129684 reaction equation
[CH3:1][N:2]([CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:3](=[O:26])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][CH:12]=2)[C:7]([CH:22]=[CH:23][C:24]#[N:25])=[CH:6]1.[Cl-].[NH4+].[N-:37]=[N+:38]=[N-:39].[Na+].C(OCC)(=O)C>CN(C)C=O>[CH3:1][N:2]([CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:3](=[O:26])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][CH:12]=2)[C:7]([CH:22]=[CH:23][C:24]2[NH:39][N:38]=[N:37][N:25]=2)=[CH:6]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 54514586HCID 54514586, compound

Product 1

HCID 178483180HCID 178483180, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 0.94 g (2 mmoles) of N-methyl-N-phenethyl-2-[5-benzyloxy-3-(2-cyanovinyl)indol-1-yl]acetamide, 0.56 g (10.45 mmoles)of ammonium chloride and 0.68 g (10.45 mmoles) of sodium azide in 20 ml of dimethyl-formamide is heated at 100° C. for 18 hours. The mixture is poured into ice water. Addition of ethyl acetate gives a precipitate which is collected and triturated in acetone to give N-methyl-N-phenethyl-2-[5-benzyloxy-3-(2-tetrazol-5-yl)vinylindol-1-yl]acetamide. (m.p. 203°-205° C.)

Workup

  1. customgives a precipitate which
  2. customis collected
  3. customtriturated in acetone

Sources & evidence

ORD record
ord-a725700d18b94f688563a8c957afa893
Source dataset
uspto-grants-1995_11
Patent number
US05468898

Reaction notes

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