1,2-Dichloroethane → 1,1-Dimethylethyl N-[2-[(3-chlorophenyl)amino]-2-oxoethyl]carbamate

HRID 410351Notes

Reaction equation

HRID 410351 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CCOCC1>ClCCl>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10](=[O:12])[NH:17][C:16]1[CH:18]=[CH:19][CH:20]=[C:14]([Cl:13])[CH:15]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79323-ChloroanilineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycine

Product 1

HCID 474512211,1-Dimethylethyl N-[2-[(3-chlorophenyl)amino]-2-oxoethyl]carbamateYield 86.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-tert-butoxycarbonyl glycine (0.5 g, 2.85 mmol) in dichloromethane (25 ml) at rt was added 3-chloroaniline (0.43 g, 3.42 mmol), HOBt (0.58 g, 4.28 mmol), EDC (1.10 g, 5.7 mmol) and N-methyl morpholine (0.43 g, 4.28 mmol). The reaction was stirred for 5 h and then washed with 1M KHSO4, 10% NaHCO3 solution and brine. The organic phase was separated, dried (Na2SO4), filtered and concentrated under reduced pressure to give [(3-chloro-phenylcarbamoyl)-methyl]-carbamic acid tert-butyl ester (0.7 g, 86%). HPLC-MS 284, 286 [M+1]+.

Workup

  1. washwashed with 1M KHSO4, 10% NaHCO3 solution and brine
  2. customThe organic phase was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f4e16ee14c204687a0958a78c80d20b8
Source dataset
uspto-grants-2014_06
Patent number
US08759520B2

Reaction notes

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