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

HRID 416131Notes

Reaction equation

HRID 416131 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-891d4d3b09324a889a457fb2d61ffb79
Source dataset
uspto-grants-2012_01
Patent number
US08088826B2

Reaction notes

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