Hydrochloric Acid → HCID 178527574, compound

HRID 232856Notes

Reaction equation

HRID 232856 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][CH2:13][CH2:14][S:15][CH:16]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH2:20][O:19][C:18]3[CH:27]=[CH:28][C:29]([O:31][CH2:32][C:33]4[CH:42]=[CH:41][C:40]5[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=5)[N:34]=4)=[CH:30][C:17]2=3)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].[N-:43]=[N+:44]=[N-:45].[Na+].[Cl-].[NH4+].Cl>CN(C)C=O>[N:34]1[C:35]2[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:41]=[CH:42][C:33]=1[CH2:32][O:31][C:29]1[CH:28]=[CH:27][C:18]2[O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH:16]([S:15][CH2:14][CH2:13][NH:12][S:9]([C:6]3[CH:5]=[CH:4][C:3]([C:1]4[NH:45][N:44]=[N:43][N:2]=4)=[CH:8][CH:7]=3)(=[O:10])=[O:11])[C:17]=2[CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 23359127HCID 23359127, compound

Product 1

HCID 178527574HCID 178527574, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

0.89 g of 11-[2-(4-cyanophenylsulfonylamino)ethylthio]-2-(quinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepine obtained in Example 34, 0.29 g of sodium azide and 0.24 g of ammonium chloride suspended in 5 ml of dimethylformamide were stirred at 120° C. for 1 hour. The reaction mixture was added to ice water and adjusted to about pH 3 with 1N-hydrochloric acid. Crystals precipitated were collected by filtration, dried and then washed with methylene chloride to obtain 0.69 g of the title compound as slightly yellow powder.

Workup

  1. customCrystals precipitated
  2. filtrationwere collected by filtration
  3. customdried
  4. washwashed with methylene chloride

Sources & evidence

ORD record
ord-84c1b0296cf743e5b0240204f3592110
Source dataset
uspto-grants-1997_01
Patent number
US05591752

Reaction notes

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