Sodium Nitrite → 6,6-Dicarboethoxy-5,6,7,8-tetrahydro-2,4(1H,3H)-quinazolinedione

HRID 22003Notes

Reaction equation

HRID 22003 reaction equation
N[C:2]1[NH:11][C:10](=[O:12])[C:9]2[CH2:8][C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:6][CH2:5][C:4]=2[N:3]=1.N([O-])=[O:24].[Na+]>C(O)(=O)C.O>[C:13]([C:7]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:6][CH2:5][C:4]2[NH:3][C:2](=[O:24])[NH:11][C:10](=[O:12])[C:9]=2[CH2:8]1)([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 135588363HCID 135588363, compound

Product 1

HCID 152840896,6-Dicarboethoxy-5,6,7,8-tetrahydro-2,4(1H,3H)-quinazolinedione

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 2-Amino-6,6-dicarboethoxy-5,6,7,8-tetrahydro-4(3H)-quinazolinone (75 g) in acetic acid (250 mL) at reflux was added a solution of sodium nitrite (75 g) in water (100 mL) in a dropwise fashion over a period of 45 min. The solution was cooled and the solvent removed in vacuo. The subsequent addition of 300 mL of water precipitated a solid which was collected and dried to yield 6,6-Dicarboethoxy-5,6,7,8-tetrahydro-2,4(1H,3H)-quinazolinedione.

Workup

  1. temperatureThe solution was cooled
  2. customthe solvent removed in vacuo
  3. additionThe subsequent addition of 300 mL of water
  4. customprecipitated a solid which
  5. customwas collected
  6. customdried

Sources & evidence

ORD record
ord-e674ad34a1b941e1a42984a68738d9d3
Source dataset
uspto-grants-1995_06
Patent number
US05426186

Reaction notes

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