Water → HCID 9799336, compound

HRID 1075389Notes

Reaction equation

[F:1][C:2]([F:10])([F:9])[C:3]([OH:8])([CH3:7])[C:4](O)=[O:5].S(Cl)(Cl)=O.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:28]=[CH:29][C:30]=1[NH2:31])[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21].O>CN(C)C(=O)C>[C:20]([C:19]1[CH:28]=[CH:29][C:30]([NH:31][C:4](=[O:5])[C:3]([OH:8])([CH3:7])[C:2]([F:10])([F:9])[F:1])=[C:17]([O:16][CH3:15])[CH:18]=1)(=[O:21])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

Conditions

Temperature: -15 °C

Procedure

To a stirred, cooled (-20° C.) solution of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (0.52 g) in N,N-dimethylacetamide (5 mL) was rapidly added thionyl chloride (0.39 g) and the mixture stirred at -10 to -20° C. for 1 hour. 3-Methoxy-4-aminobenzophenone (0.50 g) was then added in one portion and the mixture allowed to stir at room temperature overnight. The solution was poured into water and the aqueous phase decanted from the resulting oily solid. Chromatography (eluent methylene chloride then 2% ethyl ether in methylene chloride) gave the title compound (0.37 g) as an off-white solid; mp 126-128° C. Analysis for C18H16F3NO4.0.25 H2O: Calculated: C, 58.14; H, 4.47; N, 3.77; Found: C, 58.29; H, 4.48; N, 3.78.

Workup

stirringto stir at room temperature overnight
customthe aqueous phase decanted from the resulting oily solid

Sources & evidence

ORD record: ord-e83d9dd9696544318df6671d2937e5d0
Source dataset: uspto-grants-1999_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05900432

Reaction notes

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