Water → HCID 21851602, compound

HRID 617241Notes

Reaction equation

HRID 617241 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C@H:13]3[CH2:18][CH2:17][C@H:16]([OH:19])[CH2:15][CH2:14]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.O>CS(C)=O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][CH:13]3[CH2:14][CH2:15][C:16](=[O:19])[CH2:17][CH2:18]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 178521589HCID 178521589, compound

Product 1

HCID 21851602HCID 21851602, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

13.6 g of trans-4-(7-chloro-quinolin-4-ylamino)-cyclohexanol (Example 123, step 1) were dissolved in 100 ml of dimethyl sulphoxide and 68 ml of triethylamine and cooled to +10° C. under argon. A solution of 25.5 g of sulphur trioxide-pyridine complex in 100 ml of dimethyl sulphoxide was added dropwise in such a manner that the internal temperature did not exceed +15° C. After stirring for an additional 90 minutes, 800 ml of water were rapidly added dropwise. The emulsion obtained became a filterable suspension after vigourous stirring at +10° C. The filter material was recrystallized from ethanol-ether. Yield: 10.1 g (75%) of beige crystals; dec. 195° C.

Workup

  1. customdid not exceed +15° C
  2. customThe emulsion obtained
  3. stirringafter vigourous stirring at +10° C
  4. customThe filter material was recrystallized from ethanol-ether
  5. custom195° C.

Sources & evidence

ORD record
ord-5f2e1044083243f699b4f4928cf43236
Source dataset
uspto-grants-1999_09
Patent number
US05948791

Reaction notes

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