Phenyl chloroformate → HCID 59691744, compound

HRID 1811060Notes

Reaction equation

HRID 1811060 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH3:7])[N:6]=1.Cl[C:9]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:10]>C(Cl)Cl>[CH3:7][C:5]1[N:6]=[C:2]([NH:1][C:9](=[O:10])[O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:3][CH:4]=1

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 741432-Amino-4-methylthiazole

Product 1

HCID 59691744HCID 59691744, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step 1 A solution of 2-amino-4-methylthiazole (11.42 g, 0.10 mol) in DCM was cooled to 0° C. and treated with TEA (12.1 g, 0.12 mol), then phenyl chloroformate (15.6 g, 0.10 mol) was added dropwise with stirring. The mixture was stirred for 10 minutes, then was washed with NaHCO3 (aq), water and brine, and dried and concentrated. The residue was purified by column chromatography (eluting with 60:40 hexane-EtOAc) to give phenyl 4-methylthiazol-2-ylcarbamate as a white solid (12 g, 51%). 1H NMR (300 MHz, chloroform-d) δ 12.38 (bs, 1H) 7.47-7.40 (m, 2H) 7.30-7.19 (m, 3H) 6.52 (d, J=1.1 Hz, 1H) 2.41 (d, J=0.8 Hz, 3H).

Workup

  1. stirringThe mixture was stirred for 10 minutes
  2. washwas washed with NaHCO3 (aq), water and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (eluting with 60:40 hexane-EtOAc)

Sources & evidence

ORD record
ord-34199982c3bd4a8f87f324245962d704
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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