4-Toluenesulfonyl chloride → HCID 88794690, compound

HRID 1448486Notes

Reaction equation

HRID 1448486 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]2[NH:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14](=[O:15])[C:5]=2[CH2:4][O:3]1.[S:17](Cl)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]>N1C=CC=CC=1>[C:23]1([CH3:24])[CH:25]=[CH:26][C:20]([S:17]([O:15][C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6]3[C:2]([CH3:16])([CH3:1])[O:3][CH2:4][C:5]=23)(=[O:19])=[O:18])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 12593744HCID 12593744, compound

Product 1

HCID 88794690HCID 88794690, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

The compound of formula VI, 3,4-dihydro-3,3-dimethylfuro[3,4-b]quinolin-9(1H)-one (4.3 g, described in Example 8), is added portionwise to a solution of tosyl chloride (3.8 g) in dry pyridine (50 ml) at 0° C. The solution is stirred at 0° C. for 30 minutes and saturated salt solution is added. The mixture is extracted with ether and the ether extract is evaporated. Toluene is added to the residue and the solution is evaporated. The residue is crystallized from methanol to give the title compound, mp 116°-118° C.

Workup

  1. additionsaturated salt solution is added
  2. extractionThe mixture is extracted with ether
  3. extractionthe ether extract
  4. customis evaporated
  5. additionToluene is added to the residue
  6. customthe solution is evaporated
  7. customThe residue is crystallized from methanol

Sources & evidence

ORD record
ord-eeba1cd81b9b42138a13427bf6375b1a
Source dataset
uspto-grants-1979_12
Patent number
US04180580

Reaction notes

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