Urea → 6-Nitro-2,4(1H,3H)-quinazolinedione

HRID 1876182Notes

Reaction equation

HRID 1876182 reaction equation
[N+:1]([C:4]1[CH:12]=[C:8]([C:9]([OH:11])=O)[C:7]([NH2:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:14][C:15](N)=[O:16]>O>[N+:1]([C:4]1[CH:12]=[C:8]2[C:7](=[CH:6][CH:5]=1)[NH:13][C:15](=[O:16])[NH:14][C:9]2=[O:11])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 1176Urea2×HCID 120322-Amino-5-nitrobenzoic acid

Product 1

HCID 8169826-Nitro-2,4(1H,3H)-quinazolinedioneYield 90.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 5 g (27.4 mmol) of 5-nitroanthranilic acid and 22.9 g (274.0 mmol) of urea was heated to 160° C. and the melt stirred overnight. The reaction mixture was allowed to cool to 100° C. and 5 mL of water was added to dissolve the urea. The solid was filtered and suspended in 100 mL of 0.5 N NaOH and heated to boiling for 40 min to allow formation of the sodium salt. Then the mixture was cooled down and the pH was adjusted with 1 M HCl until pH=5. The precipitate was filtered off and washed with water and dried in vacuo to give 5.12 g of the title compound. 1H NMR (DMSO-d6) δ 11.7 (s, 2H), 8.6 (s, 1H), 8.45(d, 1H), 7.4 (d, 1H); LC-MS (ESI+; 208 ([M+H]+)).

Workup

  1. temperatureto cool to 100° C.
  2. filtrationThe solid was filtered
  3. temperatureheated
  4. waitto boiling for 40 min
  5. temperatureThen the mixture was cooled down
  6. filtrationThe precipitate was filtered off
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-ca8615f6273a47798d798edd0eb6318b
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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