Tetrahydrofuran → HCID 19855948, compound

HRID 2073754Notes

Reaction equation

HRID 2073754 reaction equation
O1CCCC1.[CH3:6][S:7]([NH:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([Cl:17])=[O:16])=[CH:13][CH:12]=1)(=[O:9])=[O:8].[CH2:20]([N:22]([CH2:34][CH3:35])[CH2:23][CH2:24][NH:25][C:26]1[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:27]=1[CH3:33])[CH3:21].[OH-].[NH4+]>C(#N)C>[ClH:17].[CH2:34]([N:22]([CH2:20][CH3:21])[CH2:23][CH2:24][N:25]([C:26]1[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:27]=1[CH3:33])[C:15](=[O:16])[C:14]1[CH:18]=[CH:19][C:11]([NH:10][S:7]([CH3:6])(=[O:9])=[O:8])=[CH:12][CH:13]=1)[CH3:35]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14923Ammonium HydroxideHCID 3060773HCID 3060773, compoundHCID 117911194-[(Methylsulfonyl)amino]benzoyl chloride

Product 1

HCID 19855948HCID 19855948, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 15 mL of tetrahydrofuran under nitrogen atmosphere add 0.74 g (4.7 mmol) of 4-[(methylsulfonyl)amino]benzoyl chloride then add 0.89 g (0.40 mmol) of N,N-diethyl-N'-(2,6-dimethylphenyl)-1,2-ethanediamine. When the addition is complete allow the reaction to stir at reflux. Monitor the progress of the reaction by thin-layer chromatography (concentrated aqueous ammonium hydroxide: acetonitrile, 1:9). Upon completion of the reaction, cool the mixture to room temperature. Filter the resulting solid and wash the solid with tetrahydrofuran. Recrystallize from acetonitrile to provide the title compound.

Workup

  1. additionWhen the addition
  2. customthe reaction
  3. temperatureat reflux
  4. customUpon completion of the reaction
  5. filtrationFilter the resulting solid
  6. washwash the solid with tetrahydrofuran
  7. customRecrystallize from acetonitrile

Sources & evidence

ORD record
ord-bd46b3759fbe4614aab8371a7b87183b
Source dataset
uspto-grants-1990_04
Patent number
US04920116

Reaction notes

Loading…