Diethyl Ether → HCID 10303191, compound

HRID 1057770Notes

Reaction equation

HRID 1057770 reaction equation
Cl.[CH2:2]([NH:9][CH2:10][CH2:11][C:12]([F:15])([F:14])[F:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.Cl[CH2:26][C:27]1[S:31][C:30]([NH:32][C:33]2[C:38]([Cl:39])=[CH:37][C:36]([Cl:40])=[CH:35][C:34]=2[Cl:41])=[N:29][C:28]=1[C:42]([F:45])([F:44])[F:43].CCOCC>C(Cl)Cl>[CH2:2]([N:9]([CH2:26][C:27]1[S:31][C:30]([NH:32][C:33]2[C:34]([Cl:41])=[CH:35][C:36]([Cl:40])=[CH:37][C:38]=2[Cl:39])=[N:29][C:28]=1[C:42]([F:44])([F:43])[F:45])[CH2:10][CH2:11][C:12]([F:14])([F:13])[F:15])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 81531DiisopropylethylamineHCID 12967649HCID 12967649, compoundHCID 21916307HCID 21916307, compound

Product 1

HCID 10303191HCID 10303191, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of benzyl-3,3,3-trifluoropropyl-amine hydrochloride (152.8 mg, 3 equiv.) in methylene chloride (10 mL) at room temperature was treated with diisopropylethylamine (0.132 mL, 3 equiv.). Within a few minutes the mixture became homogeneous and then a 12.5 mg/mL solution of (5-chloromethyl-4-trifluoromethyl-thiazol-2-yl)-(2,4,6-trichloro-phenyl)-amine in ether (8 mL, 0.2525 mmoles) was added all at once. After 12 hours at room temperature, the mixture was evaporated and the residue partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over sodium sulfate and evaporated. The residue was chromatographed on silica gel, eluting with 12% ethyl acetate/hexane, to give the product as a colorless glass (133.6 mg, 94%). 1H-NMR δ (CDCl3) 2.27 (m, 2H), 2.75 (ABq, 2H), 3.62 (s, 2H), 3.74 (s, 2H), 7.28 (m, 5H), 7.48 (s, 2H), 8.75 (br, 1H). Mass spec.: 563.98 (MH+).

Workup

  1. waitWithin a few minutes the mixture became homogeneous
  2. customthe mixture was evaporated
  3. customthe residue partitioned between ethyl acetate and water
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel
  8. washeluting with 12% ethyl acetate/hexane

Sources & evidence

ORD record
ord-14917b90d83b44d3ab31a02824fae4b7
Source dataset
uspto-grants-2003_02
Patent number
US06515005B2

Reaction notes

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