Sodium Hydroxide → HCID 178515536, compound

HRID 926552Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.[F:12][C:13]([F:25])([F:24])[C:14](=O)[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH-].[Na+].[NH4+].[OH-]>C(Cl)Cl>[CH2:16]([C:15]1[C:14]([C:13]([F:12])([F:25])[F:24])=[N:1][C:2]2[C:3]([C:4]=1[OH:6])=[CH:7][C:8]([I:11])=[CH:9][CH:10]=2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-amino-5-iodobenzoic acid (5.73 g, 21.8 mmol), 1,1,1-trifluoro-4-phenylbutan-2-one (5.30 g, 26.2 mmol, see reference Yang, D; Wong, M; Yan, Z. J. Org. Chem. 2000, 65, 4179-4184), and Eaton's reagent (16 mL) in a sealed pressure tube was heated at 100° C. for 1.5 hours. The reaction was then cooled to room temperature and ice-water and DCM were added. Then the pH was adjusted to pH 9 by the slow addition of 50% aqueous NaOH and concentrated NH4OH solutions (the mixture was periodically cooled in an ice-water bath to maintain the temperature below 40° C.). The precipitated solid was filtered, washed with water and Et2O, and air dried to provide the title compound as the crude product.

Workup

temperatureThe reaction was then cooled to room temperature
temperaturewas periodically cooled in an ice-water bath
temperatureto maintain the temperature below 40° C.)
filtrationThe precipitated solid was filtered
washwashed with water and Et2O, and air
customdried

Sources & evidence

ORD record: ord-d20e549258d049e7938d1d51771b3038
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284308B2

Reaction notes

Loading…