Hydrochloric Acid → HCID 11605550, compound

HRID 851988Notes

Reaction equation

HRID 851988 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=2)[CH:12]2[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][CH2:15][NH:14][C:13]2=[O:21])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl-].[NH4+].[N-:33]=[N+:34]=[N-:35].[Na+].Cl>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH:12]2[CH2:18][C:17]([CH3:19])([CH3:20])[CH2:16][CH2:15][NH:14][C:13]2=[O:21])[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[N:33]=[N:34][NH:35][N:30]=3)=[CH:25][CH:24]=2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 69491250HCID 69491250, compound

Product 1

HCID 11605550HCID 11605550, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

Rac-4-Chloro-N-(4-cyano-benzyl)-N-(5,5-dimethyl-2-oxo-azepan-3-yl)-benzenesulfonamide (80 mg, 0.18 mmol) was dissolved in dimethylformamide (1 ml). Then ammonium chloride (11 mg, 0.2 mmol) and sodium azide (13 mg, 0.2 mmol) was added and the mixture was stirred overnight at 120° C. After cooling the mixture was distributed 3 times between ethyl acetate (10 ml) and hydrochloric acid (10 ml 1N). The combined organic layers were dried and evaporated. The residue was purified on silica gel (eluent hexane/ethyl acetate) to yield 79 mg (89%). MS: m/e=506.1 (M+NH4+).

Workup

  1. temperatureAfter cooling the mixture
  2. customThe combined organic layers were dried
  3. customevaporated
  4. customThe residue was purified on silica gel (eluent hexane/ethyl acetate)
  5. customto yield 79 mg (89%)

Sources & evidence

ORD record
ord-7ae5af2878254711a101fbb695b98a8d
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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