Benzyl chloroformate → (4-Methoxy-7-phenyl-benzothiazol-2-yl)-carbamic acid benzyl ester

HRID 1060291Notes

Reaction equation

HRID 1060291 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][CH:8]=[C:7]([O:17][CH3:18])[C:5]=2[N:6]=1.Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]>N1C=CC=CC=1>[CH2:23]([O:22][C:20](=[O:21])[NH:1][C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][CH:8]=[C:7]([O:17][CH3:18])[C:5]=2[N:6]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 222830262-Amino-4-methoxy-7-phenyl-benzothiazole

Product 1

HCID 86584926(4-Methoxy-7-phenyl-benzothiazol-2-yl)-carbamic acid benzyl esterYield 79.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 2-amino-4-methoxy-7-phenyl-benzothiazole (512 mg, 2 mmol) in pyridine at 90° C. was added benzyl chloroformate (3.3 ml, 23.4 mmol) in three portions over 6 hours. The reaction mixture was then evaporated to dryness and partioned between CH2Cl2 (50 ml) and saturated aqueous NaCl solution (50 ml), the aqueous phase was separated and extracted further with CH2Cl2 (2×50 ml) and the combined organic phases dried, filtered and evaporated. The crude residue was then chromatographed over SiO2 (Merck 230-400 mesh) eluting with CH2Cl2/EtOAc (4:1) to afford the title compound as a white foam (620 mg, 79% yield), MS: m/e=391.2 (M+H+).

Workup

  1. customThe reaction mixture was then evaporated to dryness
  2. customthe aqueous phase was separated
  3. extractionextracted further with CH2Cl2 (2×50 ml)
  4. customthe combined organic phases dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude residue was then chromatographed over SiO2 (Merck 230-400 mesh)
  8. washeluting with CH2Cl2/EtOAc (4:1)

Sources & evidence

ORD record
ord-252aa20e335b4116831217cd9782eb66
Source dataset
uspto-grants-2003_02
Patent number
US06521754B2

Reaction notes

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