Pyridine → HCID 12876561, compound

HRID 444232Notes

Reaction equation

HRID 444232 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].[CH2:25]([OH:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>O1CCCC1>[CH3:1][N:2]([S:21]([O:31][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:22])[C:3](=[O:14])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:12])[CH3:13])[CH:6]=1

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 6143M-Cumenyl MethylcarbamateHCID 81031-HexanolHCID 24386Thionyl Chloride

Product 1

HCID 12876561HCID 12876561, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-isopropylphenyl methylcarbamate (3.8 g, 0.02 mol) in 20 ml anhydrous tetrahydrofuran was added 2.0 g pyridine (0.025 mol) and 2.5 g thionyl chloride (0.021 mol). The mixture was stirred for 12 hours at room temperature. Pyridine (2 g, 0.025 mol) was added and followed by 2.5 g of 1-hexanol (0.025 mol) added dropwise. Workup and purification according to procedure described for other derivatives yielded 6.5 g of the desired product (95% yield).

Workup

  1. additionadded dropwise
  2. customWorkup and purification

Sources & evidence

ORD record
ord-b2490f3adf7b48d89dc1b02cb8aa4b3a
Source dataset
uspto-grants-1981_04
Patent number
US04263318

Reaction notes

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