Diethyl Ether → Methyl benzo[d]thiazole-6-carboxylate

HRID 911323

Reaction equation

HRID 911323 reaction equation
[CH3:1]N(N=O)C(N[N+]([O-])=O)=N.C(OCC)C.[OH-].[Na+].[S:18]1[C:22]2[CH:23]=[C:24]([C:27]([OH:29])=[O:28])[CH:25]=[CH:26][C:21]=2[N:20]=[CH:19]1>C1COCC1>[CH3:1][O:28][C:27]([C:24]1[CH:25]=[CH:26][C:21]2[N:20]=[CH:19][S:18][C:22]=2[CH:23]=1)=[O:29]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 601670Benzothiazole-6-carboxylic acidHCID 135436526N-Methyl-N'-nitro-N-nitrosoguanidine

Product 1

HCID 595763Methyl benzo[d]thiazole-6-carboxylateYield 102%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 1-methyl-3-nitro-1-nitrosoguanidine (5.0 g, 33.9 mmol) to a mixture of diethyl ether (20 mL) and 1N aqueous NaOH (20 mL) at ambient temperature. Separate the organic layer and add it slowly to a solution of benzothiazole-6-carboxylic acid (1.0 g, 5.58 mmol) in THF (50 mL) at 0° C. Evaporate the solvent to obtain the desired intermediate as a yellow solid (1.1 g, 100%). MS (ES+) m/z: 194 (M+H)+.

Workup

  1. customSeparate the organic layer
  2. customEvaporate the solvent

Sources & evidence

ORD record
ord-2558141ffd684e63b19fc19e482332db
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Linked notes

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