Isoamyl Nitrite → Methyl benzo[d]thiazole-7-carboxylate

HRID 882785Notes

Reaction equation

HRID 882785 reaction equation
N(OCCC(C)C)=O.[CH3:9][O:10][C:11]([C:13]1[C:21]2[S:20][C:19](N)=[N:18][C:17]=2[CH:16]=[CH:15][CH:14]=1)=[O:12]>C1COCC1>[CH3:9][O:10][C:11]([C:13]1[C:21]2[S:20][CH:19]=[N:18][C:17]=2[CH:16]=[CH:15][CH:14]=1)=[O:12]

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 10910742Methyl 2-aminobenzo[d]thiazole-7-carboxylate

Product 1

HCID 59316815Methyl benzo[d]thiazole-7-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Isoamyl nitrite (22.0 mmol) is added to a solution of 2-amino-benzothiazole-7-carboxylic acid methyl ester (10.1 mmol) in THF (29 mL). The mixture is heated to reflux for 4 h, the solvents are removed in vacuo and the residue is purified by flash chromatography (gradient: heptane to EtOAc/heptane 4/6) to give the desired product. LC-MS: tR=0.85 min; [M+H]+=194.0.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 4 h
  3. customthe solvents are removed in vacuo
  4. customthe residue is purified by flash chromatography (gradient: heptane to EtOAc/heptane 4/6)

Sources & evidence

ORD record
ord-239e5fd71c0c41fa946b2cc602a41bda
Source dataset
uspto-grants-2012_08
Patent number
US08236801B2

Reaction notes

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