Triethylamine hydrofluoride → N-(2-tert-butyldimethysilyloxy-4-nitrophenyl)-N'-phenyl-thiourea

HRID 1956624Notes

Reaction equation

HRID 1956624 reaction equation
[Si:1]([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:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].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].[Si:1]([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:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

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

Product 2

HCID 38657231-(2-Hydroxy-4-nitrophenyl)-3-phenylthioureaHCID 15524278N-(2-tert-butyldimethysilyloxy-4-nitrophenyl)-N'-phenyl-thioureaYield 109.9%

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%). mp: 144°-145° C.;1H NMR (CD3OD/CDCl3): d 8.65 (d, 1H, J=10.0 Hz), 7.58 (d, 1H, J=10.0 Hz), 7.47 (d, 1H, J=1.25 Hz), 7.26 (m, 4H), 7.10 (m, 1H).

Workup

  1. concentrationThe solution was concentrated
  2. customflushed through a silica plug with EtOAc

Sources & evidence

ORD record
ord-bdbadd2064474710956dd6876e637ff3
Source dataset
uspto-grants-1998_07
Patent number
US05780483

Reaction notes

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