Water → HCID 19710959, compound

HRID 724784Notes

Reaction equation

HRID 724784 reaction equation
[N:1]([CH:4]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]([F:19])([F:18])[F:17])[CH:10]=2)[C:5]1=[O:20])=[N+]=[N-].C(N(CC)CC)C.O>C(S)CCS>[NH2:1][CH:4]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]([F:17])([F:18])[F:19])[CH:10]=2)[C:5]1=[O:20]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 19710983HCID 19710983, compound

Product 1

HCID 19710959HCID 19710959, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 80131,3-PropanedithiolSolvent

Procedure

A stirred solution of crude 3-azido-1-(3-trifluoromethoxyphenyl)-2-pyrrolidinone (3.50 g) in 1,3-propanedithiol (10 ml) was treated with triethylamine (4 ml). The solution was stirred for 16 hours then poured into water. The resultant mixture was extracted with diethyl ether (x3), the combined ether extracts washed with brine and dried (MgSO4). Evaporation of the solvent under reduced pressure left a yellow oil which was separated by chromatography on silica-gel, eluting with ethyl acetate followed by a 1:1 mixture of ethyl acetate and methanol, to give the sub-title compound as a clear solid (2.24 g).

Workup

  1. extractionThe resultant mixture was extracted with diethyl ether (x3)
  2. washthe combined ether extracts washed with brine
  3. dry with materialdried (MgSO4)
  4. customEvaporation of the solvent under reduced pressure
  5. waitleft a yellow oil which
  6. customwas separated by chromatography on silica-gel
  7. washeluting with ethyl acetate
  8. additionfollowed by a 1:1 mixture of ethyl acetate and methanol

Sources & evidence

ORD record
ord-db8f46d9016e4a1e8fc3dc68fe39b9de
Source dataset
uspto-grants-1998_01
Patent number
US05705456

Reaction notes

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