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

HRID 2178219Notes

Reaction equation

HRID 2178219 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-bea330e3788d4d42ad6aab41245691ac
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Reaction notes

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