Hydrochloric Acid → HCID 66826189, compound

HRID 401088Notes

Reaction equation

HRID 401088 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10])[CH:5]=O.[C:14]1([C:20](=O)[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[NH2:29][C:30]([NH2:32])=[O:31].Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:32][C:30](=[O:31])[NH:29]2)[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 99482-PhenylacetophenoneHCID 18452163HCID 18452163, compound2×

Product 1

HCID 66826189HCID 66826189, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
78 °C

Procedure

A mixture of 3-chloro-4-hydroxy-5-nitrobenzaldehyde (Intermediate 59) (150 mg, 0.74 mmol), 1,2-diphenylethanone (146.0 mg, 0.74 mmol), urea (133.9 mg, 2.23 mmol), concentrated hydrochloric acid (0.5 mL) in ethanol (3 mL) was refluxed at 78° C. for 45 h. After cooling, the mixture was evaporated and the residue was purified by preparative HPLC to give Compound 120 (129.1 mg, yield 41.4%). 1HNMR (DMSO-d6 400 MHz): δ 11.09 (s, 1H), 8.79 (s, 1H), 7.87 (d, J=2.0 Hz, 1H), 7.71 (d, J=2.0 Hz, 1H), 7.59 (s, 1H), 7.27-7.21 (m, 5H), 7.05-7.00 (m, 3H), 6.83-6.81 (m, 2H), 5.28 (d, J=2.8 Hz, 1H); MS (ESI): m/z 422.0 [M+H]+.

Workup

  1. temperatureAfter cooling
  2. customthe mixture was evaporated
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-059ba88147f9422eb7918cd439a27bad
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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