Triethylamine hydrofluoride → trans-N-(2-benzyloxycyclohexyl)-N'-(2-hydroxy-4-nitrophenyl)urea

HRID 368378Notes

Reaction equation

HRID 368378 reaction equation
[CH2:1]([O:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=1[O:28][Si](C(C)(C)C)(C)C)=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F.C(N(CC)CC)C>C(#N)C>[CH2:1]([O:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=1[OH:28])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10290782Triethylamine hydrofluorideHCID 15485711trans-N-(2-Benzyloxycyclohexyl)-N'-(2-tert-butyldimethylsilyloxy-4-nitrophenyl) urea

Product 1

HCID 15485712trans-N-(2-benzyloxycyclohexyl)-N'-(2-hydroxy-4-nitrophenyl)ureaYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of trans-N-(2-Benzyloxycyclohexyl)-N'-(2-tert-butyldimethylsilyloxy-4-nitrophenyl) urea (100 mg, 0.2 mmol) in acetonitrile (2 mL), triethylamine hydrofluoride (0.1 mL, 0.6 mmol) was added. The reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give product (73 mg, 95%). EI-MS m/z 386 (M+H)+.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-19e51050e09d4a3e9fac3f01f6720d08
Source dataset
uspto-grants-2000_10
Patent number
US06133319

Reaction notes

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