Water → HCID 52950827, compound

HRID 1521855Notes

Reaction equation

HRID 1521855 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[NH:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[OH:11][CH2:12][C:13]1[CH:14]=[C:15]([N:19]2[C:23]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=4[S:30](=[O:33])(=[O:32])[CH2:31][C:22]=3[C:21]([C:34](OCC)=[O:35])=[N:20]2)[CH:16]=[CH:17][CH:18]=1.O>C1COCC1>[N:5]1([C:34]([C:21]2[C:22]3[CH2:31][S:30](=[O:32])(=[O:33])[C:29]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:23]=3[N:19]([C:15]3[CH:14]=[C:13]([CH2:12][OH:11])[CH:18]=[CH:17][CH:16]=3)[N:20]=2)=[O:35])[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 6451240Aluminum(III) ChlorideHCID 66580822HCID 66580822, compound

Product 1

HCID 52950827HCID 52950827, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
4 °C

Procedure

To a solution of aluminium chloride (5.13 g; 38.49 mmol; 4.93 eq.) in THF (30 mL) stirred for 25 min at 4° C. is added morpholine (5.40 ml; 61.36 mmol; 7.86 eq.) and the reaction mixture is stirred at 4° C. for 1 h. Ethyl 1-[3-(hydroxymethyl)phenyl]-1,4-dihydrothiochromeno[4,3-c]pyrazole-3-carboxylate 5,5-dioxide (3.11 g; 7.81 mmol; 1 eq.) is added and the reaction mixture is allowed to warm up to rt. After 22 h, the reaction mixture is cooled down to 0° C. then water is added slowly (total volume 25 mL). After 30 min stirring, the product is extracted with DCM. The organic phase is washed with an aqueous solution of Rochelle salts (˜0.7 m; pH=5), brine then dried over MgSO4. The solvent is removed under reduced pressure to afford 3.39 g (99%) of the title compound as a pale yellow solid. HPLC (max plot) 95.6%; Rt 3.08 min. MS (ESI+): 440.0.

Workup

  1. temperatureto warm up to rt
  2. waitAfter 22 h
  3. temperaturethe reaction mixture is cooled down to 0° C.
  4. stirringAfter 30 min stirring
  5. extractionthe product is extracted with DCM
  6. washThe organic phase is washed with an aqueous solution of Rochelle salts (˜0.7 m; pH=5), brine
  7. dry with materialthen dried over MgSO4
  8. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-45c532a2ca6c44a1ab7bdfbb5a96682f
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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