Water → HCID 17173442, compound

HRID 1741062Notes

Reaction equation

HRID 1741062 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].C(N(CC)CC)C.Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19].O>ClCCl>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:18](=[O:19])[O:20][CH2:21][CH3:22])=[CH:4][C:3]=1[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 233594-Bromo-3-methylaniline

Product 1

HCID 17173442HCID 17173442, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Bromo-3-methylaniline (5.00 g, 27 mmol) and triethylamine (4.5 ml, 32 mmol) were stirred in dichloromethane (200 ml) as ethyl chloroformate (3.1 ml, 32 mmol) was added dropwise. The mixture was stirred for 2 h, when water was added. After stirring for a further 15 min, the white precipitate was filtered off, and the filtrate was separated. The organic portion was dried (Na2SO4) and evaporated to give the title compound (2.57 g, 37%) as an orange-brown oil.

Workup

  1. additionwas added dropwise
  2. stirringAfter stirring for a further 15 min
  3. filtrationthe white precipitate was filtered off
  4. customthe filtrate was separated
  5. dry with materialThe organic portion was dried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-2a0b8fb167f6470185a4d666b24750f4
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

Loading…