6-Aminobenzothiazole → 4-Nitrophenyl benzo[d]thiazol-6-ylcarbamate hydrochloride

HRID 70154Notes

Reaction equation

HRID 70154 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[CH:7][S:8][C:4]=2[CH:3]=1.[Cl:11][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]>C(Cl)Cl>[ClH:11].[S:8]1[C:4]2[CH:3]=[C:2]([NH:1][C:12](=[O:13])[O:14][C:15]3[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=3)[CH:10]=[CH:9][C:5]=2[N:6]=[CH:7]1

Participants

4

Reactant 2

HCID 682886-AminobenzothiazoleHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 667973034-Nitrophenyl benzo[d]thiazol-6-ylcarbamate hydrochlorideYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Aminobenzothiazole (100 mg, 0.666 mmol) and p-nitrophenyl chloroformate (148 mg, 0.733 mmol) were stirred at rt in CH2Cl2 (5 mL) overnight. The resulting solid was collected by filtration, yielding 183 mg (81%) of the title compound. LC-MS: RT=8.17 min, [M+H]+=316.0.

Workup

  1. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-5b5b00a8a2234c6e86c3e37c49c0c5b4
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Reaction notes

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