Hydrochloric Acid → HCID 178477875, compound

HRID 232850Notes

Reaction equation

HRID 232850 reaction equation
C[Sn]([N:5]=[N+:6]=[N-:7])(C)C.[Cl:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([CH2:19][O:20][C:21]3[CH:40]=[CH:39][C:24]4[O:25][CH2:26][C:27]5[CH:38]=[CH:37][CH:36]=[CH:35][C:28]=5[CH:29]([S:30][CH2:31][CH2:32][C:33]#[N:34])[C:23]=4[CH:22]=3)=[N:16]2)=[CH:11][CH:10]=1.Cl.[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[Cl:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([CH2:19][O:20][C:21]3[CH:40]=[CH:39][C:24]4[O:25][CH2:26][C:27]5[CH:38]=[CH:37][CH:36]=[CH:35][C:28]=5[CH:29]([S:30][CH2:31][CH2:32][C:33]5[NH:34][N:7]=[N:6][N:5]=5)[C:23]=4[CH:22]=3)=[N:16]2)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5104973Azido(trimethyl)stannaneHCID 233591442-(7-Chloroquinolin-2-yl)methoxy-11-(2-cyanoethylthio)-6,11-dihydrodibenz[b,e]oxepine

Product 1

HCID 178477875HCID 178477875, compoundYield 4.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

1.25 g of trimethyltin azide was added to 1.4 g of 2-(7-chloroquinolin-2-yl)methoxy-11-(2-cyanoethylthio)-6,11-dihydrodibenz[b,e]oxepine dissolved in 40 ml of xylene and the mixture was refluxed under heating for 8.5 hours. After cooling, 1.5 ml of conc. hydrochloric acid was added to the mixture and the mixture was stirred at room temperature for 15 minutes and then adjusted to about pH 4 with a 1N-sodium hydroxide aqueous solution. Crystals precipitated were applied to silica gel column chromatography to obtain 70 mg of the title compound as light orange powder.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 8.5 hours
  3. temperatureAfter cooling
  4. customCrystals precipitated

Sources & evidence

ORD record
ord-9c0a64eb273e4564936a45efb716099b
Source dataset
uspto-grants-1997_01
Patent number
US05591752

Reaction notes

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