Urea → HCID 59644674, compound

HRID 2252274Notes

Reaction equation

HRID 2252274 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:31]=[C:30]([C:32](=[O:36])[NH:33][CH2:34][CH3:35])[CH:29]=[CH:28][C:14]=1[O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](O)=[O:24])=[CH:18][C:17]=1[O:26][CH3:27])(=[O:11])=[O:10].[NH2:37]C(N)=O.C(=O)([O-])[O-].[Na+].[Na+]>Cl>[C:23]([CH2:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][C:14]2[CH:28]=[CH:29][C:30]([C:32]([NH:33][CH2:34][CH3:35])=[O:36])=[CH:31][C:13]=2[NH:12][S:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])(=[O:10])=[O:11])=[C:17]([O:26][CH3:27])[CH:18]=1)(=[O:24])[NH2:37]

Participants

5

Reactant 3

HCID 1176UreaHCID 10340Sodium CarbonateHCID 9872340HCID 9872340, compound

Product 1

HCID 59644674HCID 59644674, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
175 °C

Procedure

A mixture of acid 12 (70 mg, 0.126 mmol) and urea (1.0 g, 16.6 mmol) was heated to 170-180° C. and maintained at this temperature for 4 h, and the mixture was allowed to cool. As soon as the temperature dropped to 110-120° C., 2 mL of 5% sodium carbonate aqueous solution was added, and the mixture was shaken vigorously. After mixture was cooled to room temperature, 20 mL of 3N HCl aqueous solution was added and the resulting mixture was extracted with ethyl acetate (4×20 mL). The combined extracts were washed with water and brine, dried and concentrated. The residue was purified by silica gel chromatography using EtOAc and 10% CH3OH/EtOAc sequentially as the eluents to give 47 mg of product. 1H NMR (Acetone-d6): δ 8.77 (s, 1H), 8.04 (d, J=2.13 Hz, 1H), 7.96 (d, J=8.57 Hz, 1H), 7.70 (, br s, 1H), 7.63 (d, J=2.13 Hz, 1H); 7.56 (dd, J=8.53, 2.13 Hz, 1H), 7.51 (dd, J=8.53, 2.13 Hz, 1H), 7.11 (d, J=1.86 Hz, 1H), 6.88 (dd, J=8.13, 1.87 Hz, 1H), 6.85 (br s, 1H), 6.75 (d, J=8.13 Hz, 1H), 6.659 (d, J=8.67 Hz, 1H), 3.67 (s, 3H), 3.51 (s, 2H), 3.38 (m, 2H), 1.17 (dd, J=7.20, 7.20 Hz, 3H). LCMS (ESI−) 551 (M−1).

Workup

  1. temperaturemaintained at this temperature for 4 h
  2. temperatureto cool
  3. additionAs soon as the temperature dropped to 110-120° C.
  4. temperatureAfter mixture was cooled to room temperature
  5. extractionthe resulting mixture was extracted with ethyl acetate (4×20 mL)
  6. washThe combined extracts were washed with water and brine
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-186017f88db44a0c858f40870949573a
Source dataset
uspto-grants-2008_01
Patent number
US07321001B2

Reaction notes

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