Water → N-(7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)-N'-(3-iodophenyl)urea

HRID 130642Notes

Reaction equation

HRID 130642 reaction equation
[OH:1][CH:2]1[CH2:11][C:10]2[C:9]([NH:12][C:13](=[O:21])OC3C=CC=CC=3)=[CH:8][CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.[I:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=1)[NH2:26].O>CS(C)=O>[OH:1][CH:2]1[CH2:11][C:10]2[C:9]([NH:12][C:13]([NH:26][C:25]3[CH:27]=[CH:28][CH:29]=[C:23]([I:22])[CH:24]=3)=[O:21])=[CH:8][CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 122713-IodoanilineHCID 59731048Phenyl (7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)carbamate

Product 1

HCID 59731045N-(7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)-N'-(3-iodophenyl)ureaYield 47%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

Next, a mixture of phenyl (7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)carbamate (30.0 mg, 0.11 mmol) and 3-iodoaniline (25.5 mg, 0.12 mmol) in 0.2 mL of DMSO was heated at 100° C. for 16 hours. After cooled to room temperature, water was added and the product was extracted with ethylacetate. The organic layer was washed with water then brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to obtain N-(7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)-N′-(3-iodophenyl)urea (20.3 mg, 47% yield).

Workup

  1. temperatureAfter cooled to room temperature
  2. extractionthe product was extracted with ethylacetate
  3. washThe organic layer was washed with water
  4. dry with materialbrine, dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8d80bd7acd654485b34443fdea16eb68
Source dataset
uspto-grants-2008_06
Patent number
US07381840B2

Reaction notes

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