Water → 3-Amino-4,5,6,7-tetrahydrobenzo[1,2-b]selenophene-2-carboxamide

HRID 1097227Notes

Reaction equation

HRID 1097227 reaction equation
[NH2:1][C:2]1[C:3]2[CH2:12][CH2:11][CH2:10][CH2:9][C:4]=2[Se:5][C:6]=1[C:7]#[N:8].[OH-:13].[Na+].O>C(O)C>[NH2:1][C:2]1[C:3]2[CH2:12][CH2:11][CH2:10][CH2:9][C:4]=2[Se:5][C:6]=1[C:7]([NH2:8])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 595472123-Amino-4,5,6,7-tetrahydrobenzo[1,2-b]selenophene-2-carbonitrile

Product 1

HCID 595472233-Amino-4,5,6,7-tetrahydrobenzo[1,2-b]selenophene-2-carboxamideYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 3-amino-4,5,6,7-tetrahydrobenzo[1,2-b]selenophene-2-carbonitrile (2.4 g) in ethanol (50 mL) was added aqueous sodium hydroxide solution (50 mL, 10%) at rt and the mixture was refluxed for 1 h. The cooled reaction mixture was poured into ice cooled water and stirred for 15 min. The precipitated solid filtered, washed with cold water and dried to give the product as a pale brown color solid (1.4 g, 54%), mp 152-154° C. 1H NMR (400 MHz, DMSO-d6): δ 6.58 (1H, s, —CONH2), 6.45 (1H, s, —CONH2), 2.66 (2H, s, H-7), 2.24 (2H, s, H-4), 1.73 (4H, s, H-5,6); LC-MS (positive ion mode): m/z 265, 267 (M+Na)+.

Workup

  1. temperaturethe mixture was refluxed for 1 h
  2. customThe cooled reaction mixture
  3. additionwas poured into ice
  4. filtrationThe precipitated solid filtered
  5. washwashed with cold water
  6. customdried

Sources & evidence

ORD record
ord-3f6a2192ebba4248a07578a987bf48c3
Source dataset
uspto-grants-2012_03
Patent number
US08143237B2

Reaction notes

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