Trichloroethanol → HCID 178458018, compound

HRID 1930352Notes

Reaction equation

HRID 1930352 reaction equation
[C:1]([C:5]1[CH:9]=[C:8](C(O)=O)[N:7](C(C)C)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C([N:18]([CH2:21]C)CC)C.C1(P(N=[N+]=[N-])([C:31]2[CH:36]=[CH:35]C=CC=2)=O)C=CC=CC=1.[Cl:40][C:41]([Cl:45])([Cl:44])[CH2:42][OH:43].[O:46]1CCOCC1>[Cl-].[Na+].O>[C:1]([C:5]1[CH:9]=[C:8]([N:18]([CH:36]([CH3:35])[CH3:31])[C:21](=[O:46])[O:43][CH2:42][C:41]([Cl:45])([Cl:44])[Cl:40])[NH:7][N:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 8259TrichloroethanolHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 199401P,P-Diphenylphosphinic azideHCID 69297592HCID 69297592, compound

Product 1

HCID 178458018HCID 178458018, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirring solution of 3-tert-butyl-1-isopropyl-1H-pyrazole-5-carboxylic acid (7.92 g, 38 mmol) and triethylamine (5.7 g, 56 mmol) in 1,4-dioxane (80 mL) was added diphenylphosphoryl azide (12 g, 44 mmol). The resultant reaction mixture was stirred 30 min at RT. 2,2,2-Trichloroethanol (78 g, 527 mmol) was added and the reaction was heated to 100° C. After 4 h, the completed reaction was diluted with brine and extracted with EtOAc. The organic layer was washed with water, dried (MgSO4), and concentrated in vacuo. Purification of the residue by chromatography provided 2,2,2-trichloroethyl 3-tert-butyl-isopropyl-1H-pyrazol-5-ylcarbamate (4.0 g, 31% yield). 1H-NMR (400 MHz, DMSO-d6): 9.85 (s, 1 H), 5.94 (s, 1 H), 4.90 (s, 2 H), 4.37 (m, 1 H), 1.27 (d, J=7.2 Hz, 6 H), 1.18 (s, 9 H). MS (ESI) m/z: 356.1 (M+H+).

Workup

  1. customThe resultant reaction mixture
  2. temperaturethe reaction was heated to 100° C
  3. waitAfter 4 h
  4. customthe completed reaction
  5. extractionextracted with EtOAc
  6. washThe organic layer was washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customPurification of the residue by chromatography

Sources & evidence

ORD record
ord-3be9bab2f1a04624a95363dc5714b733
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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