Ammonia → HCID 21876582, compound

HRID 723786Notes

Reaction equation

HRID 723786 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]2(O)[CH2:14][CH2:13][S:12][CH2:11][CH2:10]2)=[C:4]([F:16])[CH:3]=1.Cl.O.N>C(O)(=O)C>[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]2[CH2:14][CH2:13][S:12][CH2:11][CH:10]=2)=[C:4]([F:16])[CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 962WaterHCID 9964829HCID 9964829, compound

Product 1

HCID 21876582HCID 21876582, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-(4-Amino-2,6-difluoro-phenyl)-tetrahydro-thiopyran-4-o1 (16.7 g, 68 mM) was suspended in a mixture of concentrated hydrochloric acid (200 ml), water (50 ml) and acetic acid (200 ml), BHT (50 mg) added, and the whole stirred under nitrogen at 800 for 18 hours. After cooling, the mixture was made basic by cautious addition of concentrated ammonia, and ice-water. The mixture was then extracted with diethyl ether (2×300 ml), the extracts washed with water (100 ml), brine (200 ml) and dried (magnesium sulfate). Evaporation gave the desired product as a cream solid (15.2 g).

Workup

  1. additionadded
  2. temperatureAfter cooling
  3. extractionThe mixture was then extracted with diethyl ether (2×300 ml)
  4. washthe extracts washed with water (100 ml), brine (200 ml)
  5. dry with materialdried (magnesium sulfate)
  6. customEvaporation

Sources & evidence

ORD record
ord-d567f90fb43f409d8a449f3ba5ba9c2f
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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