Triethylamine → 3-(benzyloxy)-4-bromo-5-methoxy-N-(prop-2-yn-1-yl)benzamide

HRID 1027209Notes

Reaction equation

HRID 1027209 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:19][CH3:20])[C:17]=1[Br:18])[C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH2:27]([NH2:30])[C:28]#[CH:29].C(N(CC)CC)C>CN(C=O)C.C(Cl)Cl.CCOCC>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:19][CH3:20])[C:17]=1[Br:18])[C:12]([NH:30][CH2:27][C:28]#[CH:29])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 239041PropargylamineHCID 867106053-(Benzyloxy)-4-bromo-5-methoxybenzoic acid

Product 1

HCID 867106063-(benzyloxy)-4-bromo-5-methoxy-N-(prop-2-yn-1-yl)benzamideYield 84.7%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 3-(benzyloxy)-4-bromo-5-methoxybenzoic acid (2.0 g, 5.93 mmol) and 4 drops of DMF in DCM (40 mL) was slowly added oxalyl chloride (0.57 mL, 6.52 mmol). After three hours the solvent was removed and the residue redissolved into DCM (10 mL). To this solution was slowly added a mixture of propargylamine (0.46 mL, 7.12 mmol) and triethylamine (2.5 mL, 17.8 mmol) in DCM (2 mL). After 30 minutes the solution was diluted with ether, washed with water (2×), 1 M hydrochloric acid (2×), water, saturated sodium bicarbonate, brine, dried over magnesium sulfate and concentrated to a yellow solid. The solid was triturated with diethyl ether and dried under vacuum to provide 3-(benzyloxy)-4-bromo-5-methoxy-N-(prop-2-yn-1-yl)benzamide (1.88 g) as an off-white solid. MS=374.0 (M+1).

Workup

  1. customAfter three hours the solvent was removed
  2. dissolutionthe residue redissolved into DCM (10 mL)
  3. additionTo this solution was slowly added
  4. washwashed with water (2×), 1 M hydrochloric acid (2×), water, saturated sodium bicarbonate, brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to a yellow solid
  7. customThe solid was triturated with diethyl ether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-f7c152ec1bad4ba89709a6e156946b4b
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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