Diisopropylethylamine → Methyl 4-(6-bromo-hexanoyl-amino)-3-methyl-benzoate

HRID 551165Notes

Reaction equation

HRID 551165 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](Cl)=[O:8].[NH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][C:12]=1[CH3:21].CCN(C(C)C)C(C)C>C1COCC1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][C:12]=1[CH3:21])=[O:8]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 898486-Bromohexanoyl chlorideHCID 2736799Methyl 4-amino-3-methylbenzoate

Product 1

HCID 69206251Methyl 4-(6-bromo-hexanoyl-amino)-3-methyl-benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.14 g (10 mmol) 6-bromo-hexanoylchloride in 5.0 ml THF is slowly added dropwise with stirring at ambient temperature to 1.65 g (10 mmol) methyl 4-amino-3-methyl-benzoate in 50 ml THF with 2 ml DIPEA. After 16 hours stirring at ambient temperature the mixture is evaporated down i. vac., the residue is dissolved in dichloromethane, washed twice with water and dried over sodium sulphate. The residue remaining after evaporation i. vac. is further reacted without any more purification.

Workup

  1. customis evaporated down i
  2. dissolution, the residue is dissolved in dichloromethane
  3. washwashed twice with water
  4. dry with materialdried over sodium sulphate
  5. customafter evaporation i
  6. customis further reacted without any more purification

Sources & evidence

ORD record
ord-3eaf73dd096e44b5afdb3efc9de404c1
Source dataset
uspto-grants-2011_05
Patent number
US07947700B2

Reaction notes

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