Triethylamine hydrofluoride → 1-(2-Hydroxy-4-nitrophenyl)-3-phenylthiourea

HRID 1419351Notes

Reaction equation

HRID 1419351 reaction equation
[Si]([O:8][C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[NH:18][C:19]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[S:20])(C(C)(C)C)(C)C.CCN(CC)CC.F>CC#N>[OH:8][C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[NH:18][C:19]([NH:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[S:20]

Participants

4

Reactant 2

HCID 10290782Triethylamine hydrofluorideHCID 15524278N-(2-tert-butyldimethysilyloxy-4-nitrophenyl)-N'-phenyl-thiourea

Product 1

HCID 38657231-(2-Hydroxy-4-nitrophenyl)-3-phenylthioureaYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

N-(2-Hydroxy-4-nitrophenyl)-N'-phenyl-2-thiourea was prepared by treating a solution of N-(2-tert-butyldimethysilyloxy-4-nitrophenyl)-N'-phenyl-thiourea (100 mg, 0.248 mmol) in CH3CN (1 mL) with Et3N·HF (100 uL, 0.62 mmol) in acetonitrile for 10 minutes at 23° C. The solution was concentrated and flushed through a silica plug with EtOAc to afford the desired compound as an orange solid (55 mg, 77%).

Workup

  1. customN-(2-Hydroxy-4-nitrophenyl)-N'-phenyl-2-thiourea was prepared
  2. concentrationThe solution was concentrated
  3. customflushed through a silica plug with EtOAc

Sources & evidence

ORD record
ord-029278e106594993b2edfe8611c51660
Source dataset
uspto-grants-1999_03
Patent number
US05886044

Reaction notes

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