Water → HCID 178505955, compound

HRID 1930739Notes

Reaction equation

HRID 1930739 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[N:24]=[C:25]([CH2:28][O:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[NH:26][CH:27]=3)=[CH:19][CH:18]=2)[CH:13]=[CH:12][C:10]=1[NH2:11].[C:36](Cl)(Cl)=[S:37].O>O1CCCC1.C(OCC)C>[F:8][C:9]1[CH:15]=[C:14]([CH:13]=[CH:12][C:10]=1[N:11]=[C:36]=[S:37])[O:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[N:24]=[C:25]([CH2:28][O:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[NH:26][CH:27]=2)=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10040ThiophosgeneHCID 178507749HCID 178507749, compound

Product 1

HCID 178505955HCID 178505955, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

At 23° C. and under an argon atmosphere, triethylamine (3.34 g; 0.024 mol) is added to a solution containing 2-fluoro-4-{4-[2-(phenoxymethyl)-1H-imidazol-4-yl]phenoxy}aniline (3 g, 0.008 mol) in tetrahydrofuran (120 ml). The reaction medium is cooled down to 0° C. then the thiophosgene compound (1.01 g; 0.0088 mol) is added dropwise. Stirring is maintained at this temperature for thirty minutes then the reaction medium is returned to 23° C. and stirred at this temperature for twenty minutes. 60 ml of water and 150 ml of ethyl ether are added to the reaction medium. The two phases are separated then the organic phase is washed with a saturated sodium chloride solution. The organic phase is dried over sodium sulfate, followed by concentration to dryness then the product obtained is triturated in isopentane with traces of dichloromethane. The solid obtained is filtered then dried. A yellow-coloured powder is obtained with a yield of 78%.

Workup

  1. temperatureis maintained at this temperature for thirty minutes
  2. customis returned to 23° C.
  3. stirringstirred at this temperature for twenty minutes
  4. customThe two phases are separated
  5. washthe organic phase is washed with a saturated sodium chloride solution
  6. dry with materialThe organic phase is dried over sodium sulfate
  7. concentrationfollowed by concentration to dryness
  8. customthe product obtained
  9. customis triturated in isopentane with traces of dichloromethane
  10. customThe solid obtained
  11. filtrationis filtered
  12. customthen dried
  13. customA yellow-coloured powder is obtained with a yield of 78%

Sources & evidence

ORD record
ord-0ed9b6cc3e93462f884e7425aabdfa9a
Source dataset
uspto-grants-2012_05
Patent number
US08188133B2

Reaction notes

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