Dimethylcarbamoyl Chloride → Tert-butyl (2-(3,3-dimethylureido)-4-(thiophen-2-yl)phenyl)carbamate

HRID 2201704Notes

Reaction equation

HRID 2201704 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=[CH:4][C:3]=1[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].[CH3:21][N:22]([CH3:26])[C:23](Cl)=[O:24]>N1C=CC=CC=1.C1(C)C=CC=CC=1.O>[CH3:21][N:22]([CH3:26])[C:23](=[O:24])[NH:1][C:2]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=[CH:4][C:3]=1[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18]

Participants

6

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate

Product 1

HCID 71007375Tert-butyl (2-(3,3-dimethylureido)-4-(thiophen-2-yl)phenyl)carbamateYield 81%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

To a solution of tert-butyl 2-amino-4-(thiophen-2yl)phenylcarbamate (0.12 g, 0.41 mmol, 1.0 equiv.) in pyridine (2 mL) was added a solution of dimethylcarbamic chloride (0.07 g, 0.62 mmol, 1.5 equiv.) in toluene (0.3 mL). The resulting solution was stirred at room temperature overnight. The crude residue was diluted with water (10 mL) and extracted with ethyl acetate (10 mL×2). The combined organic layers were washed with water (10 mL), dried, filtered and concentrated. The crude residue was washed with petroleum ether (5 mL) to afford tert-butyl (2-(3,3-dimethylureido)-4-(thiophen-2-yl)phenyl)carbamate (0.12 g, 80% yield).

Workup

  1. extractionextracted with ethyl acetate (10 mL×2)
  2. washThe combined organic layers were washed with water (10 mL)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washThe crude residue was washed with petroleum ether (5 mL)

Sources & evidence

ORD record
ord-dcc16291f725475f9bbdec736df3e150
Source dataset
uspto-grants-2016_06
Patent number
US09365498B2

Reaction notes

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