Ammonia → HCID 178441430, compound

HRID 568815Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[NH:7][C:6](=[O:12])[C:5]2([CH3:14])[CH3:13].[C:15](O)(=O)[C:16]([CH3:19])([CH3:18])[CH3:17].N>O>[CH3:15][C:16]([C:19]1[NH:11][C:10]2[CH:9]=[C:8]3[NH:7][C:6](=[O:12])[C:5]([CH3:14])([CH3:13])[C:4]3=[CH:3][C:2]=2[N:1]=1)([CH3:18])[CH3:17]

Participants

Conditions

Temperature: 200 °C

Procedure

Analogously to Example 11, 0.286 g. 5,6-diamino-3,3-dimethylindolin-2-one and 0.18 g. pivalic acid are heated with 3 g. polyphosphoric acid in a pre-heated bath for 30 minutes at 200° C. A further 0.18 g. pivalic acid are then added thereto and further heated for 30 minutes at 200° C. This procedure is repeated three times so that, in all, 0.9 g. pivalic acid are used with a total reaction time of 2.5 hours. After cooling, the mixture is dissolved in about 9 ml. water and adjusted to about pH 7 to 8 with concentrated aqueous ammonia solution. The precipitate obtained is filtered off with suction and washed with water to give 0.28 g. of the title compound; m.p. >300° C. For further purification, it is dissolved in a little hot ethanol, the turbid solution is treated with charcoal, the hot clear filtrate is evaporated in a vacuum and the evaporation residue is triturated with diethyl ether. One mole of the title compound thus obtained contains 1 mole of water; m.p. >300° C.

Workup

customare used with a total reaction time of 2.5 hours
temperatureAfter cooling
dissolutionthe mixture is dissolved in about 9 ml
customThe precipitate obtained
filtrationis filtered off with suction
washwashed with water
customto give 0.28 g

Sources & evidence

ORD record: ord-02bc26d9c40a47e786da39bbe89fe0fe
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04730003

Reaction notes

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