Aniline → HCID 5277304, compound

HRID 2237607Notes

Reaction equation

HRID 2237607 reaction equation
C(C1NC=CN=1)(C1NC=CN=1)=[S:2].[CH2:13]([O:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[NH2:28][C:29]1C=CC=CC=1>ClCCl>[CH2:13]([O:20][C:21]1[CH:22]=[C:23]([NH:24][C:29]([NH2:28])=[S:2])[CH:25]=[CH:26][CH:27]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 928923-BenzyloxyanilineHCID 11412697Thiocarbonyl diimidazole

Product 1

HCID 5277304HCID 5277304, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Alternatively thiocarbonyl di-imidazole (1.1 mmol, 196 mg) is added to a solution of 3-benzyloxyaniline (1 mmol, 199 mg) in dichloromethane (5 mL). The reaction is stirred at room temperature until the aniline is consumed, about 1 hour. A solution of methanolic ammonia (2 M, 2 mL) is added and the stirring continued for 2 hours. Solvent is evaporated and the residue purified by chromatography on silica gel to give 150 mg of (3-benzyloxyphenyl)thiourea.

Workup

  1. customis consumed, about 1 hour
  2. additionA solution of methanolic ammonia (2 M, 2 mL) is added
  3. customSolvent is evaporated
  4. customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7afe6ed2fc0e499686d88f6f91ad6239
Source dataset
uspto-grants-2010_05
Patent number
US07718671B2

Reaction notes

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