Triethylamine → 1-(4-Tert-butyldimethylsiloxy-3,5-dichlorophenyl)-3-(2,6-difluorobenzoyl)urea

HRID 37327Notes

Reaction equation

HRID 37327 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]([NH:13][C:14](=[O:23])[C:15]2[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=2[F:22])=[O:12])[CH:5]=[C:6]([Cl:9])[C:7]=1[OH:8].C(N(CC)CC)C.[C:31]([Si:35](Cl)([CH3:37])[CH3:36])([CH3:34])([CH3:33])[CH3:32]>CN(C)C=O.C(OCC)(=O)C>[O:8]([C:7]1[C:2]([Cl:1])=[CH:3][C:4]([NH:10][C:11]([NH:13][C:14](=[O:23])[C:15]2[C:16]([F:22])=[CH:17][CH:18]=[CH:19][C:20]=2[F:21])=[O:12])=[CH:5][C:6]=1[Cl:9])[Si:35]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:37])[CH3:36]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 14275603HCID 14275603, compound

Product 1

HCID 190729021-(4-Tert-butyldimethylsiloxy-3,5-dichlorophenyl)-3-(2,6-difluorobenzoyl)ureaYield 65.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Into a homogeneous solution of 1-(3,5-dichloro-4-hydroxyphenyl)-3-(2,6-difluorobenzoyl)urea (3.13 grams, 8.66 mmol) in dimethylformamide (25 milliliters) was added triethylamine (1.75 grams, 17.3 mmol), and the resulting mixture was stirred for 5 minutes. Tertiary-butyldimethylsilyl chloride (3.92 grams, 26.0 mmol) was then added, and a thick precipitate formed immediately. This heterogeneous mixture was then diluted with ethyl acetate (200 milliliters), washed with saturated sodium bicarbonate (twice with 150 milliliters) and then washed with a brine solution (150 milliliters). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a brown solid. The solid was washed with cold ether and vacuum dried to afford 1-(4-tert-butyldimethylsiloxy-3,5-dichlorophenyl)-3-(2,6-difluorobenzoyl)urea (2.71 grams, 5.70 mmol) having a melting point of 184° C.-186° C. Elemental analysis of the product indicated the following:

Workup

  1. customa thick precipitate formed immediately
  2. washwashed with saturated sodium bicarbonate (twice with 150 milliliters) and
  3. washthen washed with a brine solution (150 milliliters)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a brown solid
  8. washThe solid was washed with cold ether and vacuum
  9. customdried

Sources & evidence

ORD record
ord-8346b002bf8a41d6bf780cd1df85aa57
Source dataset
uspto-grants-1995_05
Patent number
US05420163

Reaction notes

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