Trichloroethanol → HCID 69036822, compound
Reaction equation
[C:1]([C:5]1[CH:9]=[C:8](C(O)=O)[N:7]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C1C=CC(P([N:34]=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.[Cl:37][C:38]([Cl:42])([Cl:41])[CH2:39][OH:40].[O:43]1[CH2:48]COCC1>[Cl-].[Na+].O>[C:1]([C:5]1[CH:9]=[C:8]([NH:34][C:48](=[O:43])[O:40][CH2:39][C:38]([Cl:42])([Cl:41])[Cl:37])[N:7]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)[N:6]=1)([CH3:2])([CH3:3])[CH3:4]Participants
Procedure
To a stirring solution of 3-tert-butyl-1-(3-fluorophenyl)-1H-pyrazole-5-carboxylic acid (0.26 g, 0.60 mmol) and TEA (0.13 ml, 0.90 mmol) in 1,4-dioxane (9 ml) was added DPPA (0.16 ml, 0.75 mmol), After stirring for 30 min at RT, 2,2,2-trichloroethanol (0.58 ml, 6.0 mmol) was added and the reaction was heated at 100° C. for 2 h. The reaction mixture was diluted with brine (10 ml) and extracted with EtOAc (3×20 ml). The combined organic phases were washed with 5% citric acid (10 ml), satd. NaHCO3 (10 ml), dried (MgSO4), filtered and evaporated. The crude product was purified by chromatography to afforded 2,2,2-trichloroethyl 3-tert-butyl-1-(3-fluorophenyl)-1H-pyrazol-5-ylcarbamate (0.180 g, 73% yield) as colorless oil. MS (ESI) m/z: 410(M+H+).
Workup
- temperaturethe reaction was heated at 100° C. for 2 h
- extractionextracted with EtOAc (3×20 ml)
- washThe combined organic phases were washed with 5% citric acid (10 ml)
- dry with materialNaHCO3 (10 ml), dried (MgSO4)
- filtrationfiltered
- customevaporated
- customThe crude product was purified by chromatography
Sources & evidence
- ORD record
- ord-84d714f6ebcb4b45b9c2040e63b50750
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188113B2
Reaction notes
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