Pyridine → HCID 12959997, compound

HRID 1660519Notes

Reaction equation

HRID 1660519 reaction equation
[CH3:1][NH:2][C:3](=[O:14])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[CH:6]=1.N1C=CC=CC=1.[S:21](Cl)(Cl)=[O:22].[CH3:25][NH:26][S:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[O:29])=[O:28].C(N(CC)CC)C>O1CCCC1>[C:30]1([S:27]([N:26]([CH3:25])[S:21]([N:2]([CH3:1])[C:3](=[O:14])[O:4][C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:12])[CH3:13])[CH:6]=2)=[O:22])(=[O:29])=[O:28])[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

7

Reactant 5

HCID 1049PyridineHCID 6143M-Cumenyl MethylcarbamateHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 78858N-Methylbenzenesulfonamide

Product 1

HCID 12959997HCID 12959997, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-isopropylphenyl methylcarbamate (3.9 g, 0.02 mol) in dry tetrahydrofuran (15 ml), was added pyridine (2.0 g, 0.025 mol) and thionyl chloride (2.5 g, 0.021 mol). The mixture was stirred at room temperature for 4 hours. Pyridine hydrochloride was filtered rapidly and N-methylbenzenesulfonamide (3.5 g, 0.02 mol) was added. The mixture was cooled in an ice-water bath and triethylamine (2.2 g, 0.022 mol) was added dropwise. After the complete addition of the amine the mixture was stirred at room temperature for an additional half hour.

Workup

  1. filtrationPyridine hydrochloride was filtered rapidly
  2. temperatureThe mixture was cooled in an ice-water bath
  3. stirringwas stirred at room temperature for an additional half hour

Sources & evidence

ORD record
ord-68a5def4e13b41fdbedbc2649cae664b
Source dataset
uspto-grants-1981_12
Patent number
US04308274

Reaction notes

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