Aniline → HCID 178528033, compound

HRID 847400Notes

Reaction equation

HRID 847400 reaction equation
[CH2:1]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](O)=[Se:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>ClCCl>[CH2:1]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[Se:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 178526205HCID 178526205, compound

Product 1

HCID 178528033HCID 178528033, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of 6 g (0.0206 mol) 2-benzylselenobenzoic acid in 60 ml dichloromethane is treated at -10° C. with 2.64 g (0.0206 mol) chloromethylenedimethyliminium chloride (Vilsmeier's reagent). After stirring for 30 minutes at 0° C. the clear reaction mixture is treated dropwise within 15 min with a solution of 1.9 g (0.04 mol) aniline and 4.21 g (0.0416 mol) triethylamine in 60 ml dichloromethane. After stirring for 48 h at room temperature the clear yellow solution is extracted with 1N HCl (100 ml) followed by water until it is neutral, the organic phase is dried over Na2SO4 and then evaporated to dryness in vacuum. The solid crude product is recrystallized from 2-propanol (220 ml).

Workup

  1. stirringAfter stirring for 48 h at room temperature the clear yellow solution
  2. extractionis extracted with 1N HCl (100 ml)
  3. dry with materialthe organic phase is dried over Na2SO4
  4. customevaporated to dryness in vacuum
  5. customThe solid crude product is recrystallized from 2-propanol (220 ml)

Sources & evidence

ORD record
ord-1bf82347602740e68736b7f120f08a6e
Source dataset
uspto-grants-1992_08
Patent number
US05141955

Reaction notes

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