Benzenamine, 3-ethynyl- → HCID 16733971, compound

HRID 2423007Notes

Reaction equation

HRID 2423007 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:16][C:17](=[O:19])[CH3:18])=[C:9]([O:12][C:13](=[O:15])[CH3:14])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[C:20]([C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25])#[CH:21]>>[ClH:1].[C:20]([C:22]1[CH:23]=[C:24]([NH:25][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:16][C:17](=[O:19])[CH3:18])=[C:9]([O:12][C:13](=[O:15])[CH3:14])[CH:10]=3)[N:5]=[CH:4][N:3]=2)[CH:26]=[CH:27][CH:28]=1)#[CH:21]

Participants

3

Reactant 2

HCID 104682Benzenamine, 3-ethynyl-HCID 272813774-Chloroquinazoline-6,7-diyl diacetate

Product 1

HCID 16733971HCID 16733971, compoundYield 76.3%

Conditions

Temperature
27.5 °C

Procedure

Into a 2.0 L four necked round-bottomed flask, equipped with a mechanical stirrer; reflux condenser and thermometer socket are charged the above organic layer containing 4-chloro-6,7-diacetoxy-quinazoline and 3-ethynylaniline (12 g). The reaction mass was slowly heated to reach reflux condition and maintained at reflux for 14 hours and the reaction was found to be over by HPLC. Then the reaction was cooled to 25-30° C. and filtered the mass, washed the cake with chloroform, and dried to get 29 g (76.3% by theory) of N-(3-ethynylphenyl)-6,7-diacetoxy-4-quinazolinamine hydrochloride as yellow solid.

Workup

  1. temperaturereflux condenser
  2. additionthermometer socket are charged the above organic layer
  3. temperatureThe reaction mass was slowly heated
  4. temperatureto reach reflux condition
  5. temperaturemaintained
  6. temperatureat reflux for 14 hours
  7. filtrationfiltered the mass
  8. washwashed the cake with chloroform
  9. customdried

Sources & evidence

ORD record
ord-58a18d8468a549e8aa2c09c613a33f1c
Source dataset
uspto-grants-2011_06
Patent number
US07960545B2

Reaction notes

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