Phenyl chloroformate → HCID 87536672, compound

HRID 2068008Notes

Reaction equation

HRID 2068008 reaction equation
Cl.[CH2:2]([S:5]([CH2:8][C:9]1[N:10]=[C:11]([NH2:14])[S:12][CH:13]=1)(=[O:7])=[O:6])[CH2:3][CH3:4].Cl[C:16]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:17]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1.C1COCC1>[C:19]1([O:18][C:16](=[O:17])[NH:14][C:11]2[S:12][CH:13]=[C:9]([CH2:8][S:5]([CH2:2][CH2:3][CH3:4])(=[O:6])=[O:7])[N:10]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 2

HCID 15891Phenyl chloroformateHCID 131730039HCID 131730039, compound

Product 1

HCID 87536672HCID 87536672, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of 4-(propylsulfonylmethyl)thiazol-2-amine HCl-salt (3.99 g, 15.5 mmol) and DMAP (5 mol %, 95 mg) in pyridine (30 mL) was added a solution of phenyl chloroformate (1 eq, 1.96 mL) in THF (30 mL) drop wise. The reaction mixture was stirred at room temperature overnight and poured onto ice/water. The mixture was allowed to warm to room temperature and the solids were filtered off. The solids were washed with water, 10% aq. sodium bicarbonate, and dried in vacuo affording the title phenyl carbamate (1.22 g, 51% yield) as a solid.

Workup

  1. additionpoured onto ice/water
  2. temperatureto warm to room temperature
  3. filtrationthe solids were filtered off
  4. washThe solids were washed with water, 10% aq. sodium bicarbonate
  5. customdried in vacuo

Sources & evidence

ORD record
ord-5a21b8f8f72f47928adacd12f19dc8c6
Source dataset
uspto-grants-2012_10
Patent number
US08293919B2

Reaction notes

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