Hydrochloric Acid → HCID 13326265, compound

HRID 648171Notes

Reaction equation

HRID 648171 reaction equation
N[C:2]1[N:7]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:16])[C:6](=[O:17])[NH:5][C:4](=[O:18])[CH:3]=1.[ClH:19].N([O-])=O.[Na+]>O>[Cl:19][C:2]1[N:7]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:16])[C:6](=[O:17])[NH:5][C:4](=[O:18])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 13326264HCID 13326264, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 13326265HCID 13326265, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1 mole of 6-amino-1-(2,6-dimethylanilino)-2,4-pyrimidinedione dissolved in 3 moles of dilute aqueous hydrochloric acid cooled to 0°-5° in an ice bath is slowly added 1.1 mole of sodium nitrite (dissolved in water at 5°) with rapid stirring. After addition is complete, add dropwise but rapidly 1.1 mole cuprous chloride dissolved in water. Stir for 30 minutes, then heat to 50° for 1 hour. The mixture is cooled to RT and filtered to obtain 6-chloro-1-(2,6-dimethylanilino)-2,4-pyrimidinedione.

Workup

  1. temperaturecooled to 0°-5° in an ice bath
  2. additionAfter addition
  3. additionadd dropwise
  4. temperatureheat to 50° for 1 hour
  5. filtrationfiltered

Sources & evidence

ORD record
ord-40a84cabc586453ba58c5e59f0a1ba1a
Source dataset
uspto-grants-1983_10
Patent number
US04411839

Reaction notes

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