Triethylamine → HCID 21469107, compound

HRID 1938165Notes

Reaction equation

HRID 1938165 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([C:14]([NH2:17])=[CH:15][CH:16]=1)[C:5]([NH:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[O:6].C(N(CC)CC)C.[Br:25][CH2:26][C:27](Br)=[O:28]>ClCCl>[I:1][C:2]1[CH:3]=[C:4]([C:14]([NH:17][C:27](=[O:28])[CH2:26][Br:25])=[CH:15][CH:16]=1)[C:5]([NH:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 21469060HCID 21469060, compound

Product 1

HCID 21469107HCID 21469107, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

21.0 g (60.5 mmol) of 3-iodo-6-amino-N-(2-methoxycarbonylethyl)benzamide prepared as in Example 1b) were dissolved in 270 ml of dichloromethane, and 12.5 ml (90.7 mmol) of triethylamine were added. At -30° C., 7.8 ml (90.7 mmol) of bromoacetyl bromide in 80 ml of dichloromethane were added dropwise. The mixture was stirred at room temperature for 2 h and then washed with 10% strength citric acid solution and sodium bicarbonate solution, dried and concentrated. The product was recrystallized from dichloromethane, resulting in 26.1 g (92%) of pale yellow crystals.

Workup

  1. washwashed with 10% strength citric acid solution and sodium bicarbonate solution
  2. customdried
  3. concentrationconcentrated
  4. customThe product was recrystallized from dichloromethane

Sources & evidence

ORD record
ord-38aaf58a733a4116a4f61ab15dea8f84
Source dataset
uspto-grants-1997_12
Patent number
US05693637

Reaction notes

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