Dimethylformamide → HCID 21289483, compound

HRID 978771Notes

Reaction equation

HRID 978771 reaction equation
N(OC(C)(C)C)=O.CN(C)C=O.N[C:14]1[S:15][C:16]([CH2:19][C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[CH2:26][CH:25]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:24][CH2:23]3)=[CH:17][N:18]=1>C(OCC)(=O)C>[S:15]1[C:16]([CH2:19][C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[CH2:26][CH:25]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:24][CH2:23]3)=[CH:17][N:18]=[CH:14]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10906Tert-Butyl nitriteHCID 13882834HCID 13882834, compound

Product 1

HCID 21289483HCID 21289483, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 0.49 g of tertiary butyl nitrite and 5 ml of dimethylformamide was heated at 50° C. and then 1.0 g of ethyl 6-(2-amino-5-thiazolylmethyl)-1,2,3,4-tetrahydro-2-naphthalenecarboxylate was added portionwise thereto. The resulting mixture was stirred at 60° C. for 1 hour. After cooling, ethyl acetate was added to the reaction mixture and the mixture was washed with water and dried and then concentrated in vacuo. The residue was purified by silica gel column chromatography using a mixture of methanol and chloroform (1:50 by volume) for elution to give 720 mg of ethyl 6-(5-thiazolylmethyl)-1,2,3,4-tetrahydro-2-naphthalenecarboxylate as an oil.

Workup

  1. temperatureAfter cooling
  2. washthe mixture was washed with water
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. additiona mixture of methanol and chloroform (1:50 by volume)
  7. washfor elution

Sources & evidence

ORD record
ord-506138b02be544068add514519fc7dcc
Source dataset
uspto-grants-1987_05
Patent number
US04665188

Reaction notes

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