Pyridine → 4-Nitrophenyl benzo[d]thiazol-2-ylcarbamate

HRID 1896568Notes

Reaction equation

HRID 1896568 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.Cl[C:12]([O:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)=[O:13].N1C=CC=CC=1>C(Cl)Cl>[S:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[NH:1][C:12](=[O:13])[O:14][C:15]1[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 8706Benzo(d)thiazol-2-amineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 594186764-Nitrophenyl benzo[d]thiazol-2-ylcarbamateYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

The title compound 4-nitrophenyl benzo[d]thiazol-2-ylcarbamate (19) was prepared by the following procedure: To 2-aminobenzothiazole (5.0 g, 30 mmol) was added DCM (36 mL) and the reaction mixture was stirred at 0° C. for 15 minutes. Then, p-nitrophenyl chloroformate (6.64 g, 33 mmol) in DCM (60 mL) was added, followed by pyridine (2.66 mL, 33 mmol) in DCM (36 mL). The reaction mixture was stirred and allowed to warm to rt overnight. The reaction mixture was filtered, washed with DCM, and dried to provide 9.22 g (90%) of the desired product 4-nitrophenyl benzo[d]thiazol-2-ylcarbamate (19): LC/MS (APCI): m/z 316.0 (M+H).

Workup

  1. customThe title compound 4-nitrophenyl benzo[d]thiazol-2-ylcarbamate (19) was prepared by the following procedure
  2. stirringThe reaction mixture was stirred
  3. temperatureto warm to rt overnight
  4. filtrationThe reaction mixture was filtered
  5. washwashed with DCM
  6. customdried

Sources & evidence

ORD record
ord-ed1c3f7e5bfe4ebba86fba58fa6ff3a4
Source dataset
uspto-grants-2013_08
Patent number
US08518970B2

Reaction notes

Loading…