Chloride → HCID 10179336, compound

HRID 1068998Notes

Reaction equation

HRID 1068998 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:19])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.C(N([CH:25]([CH3:27])C)C)(C)C.[Cl-:28].[C:29](=[O:32])(O)[O-].[Na+]>O1CCCC1.[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:29](=[O:32])/[CH:27]=[CH:25]/[Cl:28])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 312ChlorideHCID 516892Sodium BicarbonateHCID 547370N,N-DiisopropylmethylamineHCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamine

Product 1

HCID 10179336HCID 10179336, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 2.2 g of N-(3-bromophenyl)-4,6-quinazolindiamine and 1.13 g of diisopropyl methylamine in 25 mL of tetrahydrofuran was cooled in an ice bath as 1.0 g of 3-cis-chloroacryoyl chloride was added over 5 min. After stirring and cooling for 30 min and stirring at room temperature for another 30 min, the mixture was poured into a mixture of brine and saturated sodium bicarbonate. The mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and the solvent was removed at reduced pressure. The residue was chromatographed on silica gel eluting with chloroform and ethyl acetate mixtures to give N-[4-[(3-bromophenyl)amino]-6-quinazolinyl]-3(E)-chloro-2-propenamide as a yellowish solid. mass spectrum (m/e): M+H 404.7.

Workup

  1. additionwas added over 5 min
  2. temperaturecooling for 30 min
  3. stirringstirring at room temperature for another 30 min
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customthe solvent was removed at reduced pressure
  7. customThe residue was chromatographed on silica gel eluting with chloroform and ethyl acetate mixtures

Sources & evidence

ORD record
ord-df04b0b0e5e44f09bf13a1e7adbde268
Source dataset
uspto-grants-2001_06
Patent number
US06251912B1

Reaction notes

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