Dimethylcarbamoyl Chloride → HCID 22027791, compound

HRID 1791126Notes

Reaction equation

HRID 1791126 reaction equation
[C:1]([O:5][C:6]([O:8][NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:26][N:27]([CH3:31])[C:28](Cl)=[O:29].CCOC(C)=O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([O:5][C:6]([O:8][NH:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][C:28]([N:27]([CH3:31])[CH3:26])=[O:29])=[CH:16][CH:17]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 22027819HCID 22027819, compound

Product 1

HCID 22027791HCID 22027791, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

N-t-butoxycarbonyloxy 2-(4-hydroxyphenyl)ethylamine (2.53 g, 10.7 mmol), Et3N (2.96 mL, 2 eq.), a catalytic amount of DMAP (131 mg) and dimethylcarbamyl chloride (2.0 mL, 2 eq.) are mixed in CH2Cl2 at 0° C. The resulting mixture is stirred overnight. EtOAc is added to dilute the reaction mixture and then is washed with 1N HCl, sat. Na2CO3 and brine. Solvent is removed under reduced pressure to give pure t-butoxycarbonyloxy 2-[4-(N,N-dimethylaminocarbonyloxy)phenyl]ethylamine as a colorless solid.

Workup

  1. additionto dilute the reaction mixture
  2. washis washed with 1N HCl, sat. Na2CO3 and brine
  3. customSolvent is removed under reduced pressure

Sources & evidence

ORD record
ord-451df465c903453589d5e1a3fac260c1
Source dataset
uspto-grants-2006_07
Patent number
US07074783B2

Reaction notes

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