Hydrochloric Acid → Carbamic acid, (4-ethynylphenyl)-, 1,1-dimethylethyl ester (9CI)

HRID 2089563Notes

Reaction equation

HRID 2089563 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.CCN(CC)CC.[O:17](C(OC(C)(C)C)=O)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=O.Cl>C(Cl)Cl>[C:18]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 37600254-Ethynylaniline

Product 1

HCID 12121165Carbamic acid, (4-ethynylphenyl)-, 1,1-dimethylethyl ester (9CI)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

p-Aminophenyl-acetylene (1.17 g, 10 mmol) was added to DCM (30 mL), and Et3N (2.8 mL, 20 mmol) was added thereto. (BOC)2O (2.3 g, 10 mmol) was added, and the mixture was stirred for 2 h at room temperature. After completion of the reaction, 1N HCl was added, which was then extracted with EtOAc and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound.

Workup

  1. additionwas added
  2. additionwas added
  3. extractionwhich was then extracted with EtOAc
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was removed under reduced pressure
  7. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4bbd49a03ff045d1a64443734c3499c9
Source dataset
uspto-grants-2013_05
Patent number
US08436038B2

Reaction notes

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