Potassium Carbonate → HCID 19365941, compound

HRID 850096Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:25])([C:16]([C:18]1[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=1)=[CH2:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.[C:26](=[O:29])([O-])[O-].[K+].[K+].[Na+].[Na+].C(N(CC(O)=O)CC(O)=O)C[N:36](CC([O-])=O)CC([O-])=O>O.[Cu].C(N)=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:25])([C:16]([C:18]1[CH:23]=[CH:22][C:21]([NH:36][CH:26]=[O:29])=[CH:20][CH:19]=1)=[CH2:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

Conditions

Temperature: 140 °C

Procedure

An intimate mixture of 2-(2,4-difluorophenyl)-3-(4-iodophenyl)-1-(1,2,4-triazol-1-yl)-3-buten-2-ol (12 g, 26 mmol-see Preparation 20), formamide (18 ml, 0.25 mmol), copper (3.6 g, 57 mmol) and potassium carbonate (6.0 g, 43 mmol) was heated, with stirring, to 140° C. for 2 hours. The mixture was cooled to 100° C. and treated with a suspension of ethylenediaminetetracetic acid disodium salt (25 g, 6.7 mmol) in water (250 ml). After further cooling to room temperature, the mixture was extracted with dichloroniethane (2×200 ml). The combined organic extracts were dried (MgSO4) and evaporated under reduced pressure to give 2-(2,4-difluorophenyl)-3-(4-formamidophenyl)-1-(1,2,4-triazol-1-yl)but-3-en-2-ol (5.3 g, 55%), which was used crude in the next step.

Workup

temperaturewas heated
temperatureThe mixture was cooled to 100° C.
temperatureAfter further cooling to room temperature
extractionthe mixture was extracted with dichloroniethane (2×200 ml)
dry with materialThe combined organic extracts were dried (MgSO4)
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-332fddac3ecd40f5b042fc4963d717e6
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06015825

Reaction notes

Loading…