Ammonia → HCID 54351421, compound

HRID 1655496Notes

Reaction equation

HRID 1655496 reaction equation
Cl[S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13](=[O:20])[C:14](=[N+:18]=[N-:19])[C:15](=[O:17])[CH3:16])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[NH3:21]>C(#N)C>[NH2:21][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13](=[O:20])[C:14](=[N+:18]=[N-:19])[C:15](=[O:17])[CH3:16])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 53743745HCID 53743745, compound2×

Product 1

HCID 54351421HCID 54351421, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 6-(4-chlorosulfonylphenyl)-3-diazo-2,4-hexanedione (1.0 g, 3.2 mmol) obtained in Example 3, (3) in acetonitrile (5 ml), 28% aqueous ammonia (2 g) was added dropwise at 5°-10° C., and stirring was continued for 6 h at room temperature. Then the mixture was evaporated under reduced pressure and the residue was chromatographed on silica gel (Wako Gel C-200; manufactured by Wako Pure Chemical Industries, Ltd.) with n-hexane/ethyl acetate (from 5:1 to 2:1) as eluent to give the title compound as a white amorphous solid; yield: 800 mg; mp 109.5°-111.5° C.

Workup

  1. customThen the mixture was evaporated under reduced pressure
  2. customthe residue was chromatographed on silica gel (Wako Gel C-200; manufactured by Wako Pure Chemical Industries, Ltd.) with n-hexane/ethyl acetate (from 5:1 to 2:1) as eluent

Sources & evidence

ORD record
ord-9d9cc82d5ddb40788626ffa27417975d
Source dataset
uspto-grants-1993_10
Patent number
US05250669

Reaction notes

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