Trichloroethanol → HCID 67253670, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][CH:15]=[CH:14]3)=[C:6]([CH:10]=1)C(O)=O.C1C=CC(P([N:35]=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.[Cl:38][C:39]([Cl:43])([Cl:42])[CH2:40][OH:41].[O:44]1[CH2:49]COCC1>[Cl-].[Na+].O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][CH:15]=[CH:14]3)=[C:6]([NH:35][C:49](=[O:44])[O:41][CH2:40][C:39]([Cl:43])([Cl:42])[Cl:38])[CH:10]=1Participants
6
Procedure
To a stirring solution of 5-chloro-2-(quinolin-6-yl)benzoic acid (0.201 g, 0.708 mmol) and TEA (0.148 ml, 1.06 mmol) in 1,4-dioxane (10 ml) at RT, was added DPPA (0.191 ml, 0.244 mmol). After stirring for 30 min at RT, 2,2,2-trichloroethanol (0.680 ml, 7.08 mmol) was added and the reaction was stirred with heating at 100° C. for 2 h. The completed reaction was diluted with brine (10 ml) and extracted with EtOAc (3×25 ml). The combined organics were washed with 5% citric acid (10 ml), sat'd. NaHCO3 (10 ml) and brine (10 ml), dried (MgSO4), concentrated in vacuo and purified by chromatography to afford 2,2,2-trichloroethyl 5-chloro-2-(quinolin-6-yl)phenylcarbamate (0.25 g, 82% yield) as a white solid. MS (ESI) m/z: 431.0 (M+H+).
Workup
- stirringthe reaction was stirred
- temperaturewith heating at 100° C. for 2 h
- customThe completed reaction
- extractionextracted with EtOAc (3×25 ml)
- washThe combined organics were washed with 5% citric acid (10 ml)
- dry with materialNaHCO3 (10 ml) and brine (10 ml), dried (MgSO4)
- concentrationconcentrated in vacuo
- custompurified by chromatography
Sources & evidence
- ORD record
- ord-3b20860b99664528a738484f58e5f12b
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07790756B2
Reaction notes
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