Ammonium Chloride → HCID 68724707, compound

HRID 2093649Notes

Reaction equation

HRID 2093649 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[O:11][C:12]([F:15])([F:14])[F:13].F[P-](F)(F)(F)(F)F.[N:23]1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.O.OC1C2N=NNC=2C=CC=1.C(N(C(C)C)CC)(C)C.[Cl-].[NH4+]>CN(C)C=O.C(OCC)(=O)C>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:23])=[O:7])=[CH:4][C:3]=1[O:11][C:12]([F:15])([F:14])[F:13]

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 58182218HCID 58182218, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 68724707HCID 68724707, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-hydroxy-3-(trifluoromethoxy)benzoic acid (841 mg, 3.79 mmol) in dimethylformamide (10 ml) were added (benzotriazol-1-yloxy)tris(dimethylamino) phosphonium hexafluorophosphate (1.84 g, 4.17 mmol), hydroxybenzotriazole hydrate (563 mg, 4.17 mmol), diisopropylethylamine (1.99 ml, 11.4 mmol), and ammonium chloride (405 mg, 7.58 mmol). The resulting solution was stirred at room temperature for 2 h, and then diluted with ethyl acetate and washed with 0.5 M HCl and brine (2×). The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography using a Horizon Biotage, 65i Si column, eluting with 1 column volume of dichloromethane, followed by a linear gradient of ethyl acetate in dichloromethane from 0% to 100% over 10 column volumes to afford the title compound. Mass spectrum (ESI) 222.1 (M+1).

Workup

  1. washwashed with 0.5 M HCl and brine (2×)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography
  5. washeluting with 1 column volume of dichloromethane

Sources & evidence

ORD record
ord-4a912f9bfff34ec28605a4e5808851fe
Source dataset
uspto-grants-2013_05
Patent number
US08445480B2

Reaction notes

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