Oxalyl chloride → HCID 53706173, compound

HRID 1900677Notes

Reaction equation

HRID 1900677 reaction equation
C(Cl)(=O)C(Cl)=O.OCC[O:10][C:11]1[N:20]=[C:19]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]3[O:29][CH2:30][O:31][C:25]=3[CH:24]=2)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:32]#[N:33])[CH:17]=2)[N:12]=1.C(N(CC)[CH:38]([CH3:40])[CH3:39])(C)C.[CH2:43]([O:45][C:46](C=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:47])[CH3:44]>CS(C)=O.O.C(Cl)Cl>[CH2:43]([O:45][C:46]([CH:40]=[CH:38][CH2:39][O:10][C:11]1[N:20]=[C:19]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]3[O:29][CH2:30][O:31][C:25]=3[CH:24]=2)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:32]#[N:33])[CH:17]=2)[N:12]=1)=[O:47])[CH3:44]

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 81531DiisopropylethylamineHCID 18980309HCID 18980309, compound

Product 1

HCID 53706173HCID 53706173, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

250 μl of dimethyl sulfoxide was slowly dropped into a mixture comprising 150 μl of oxalyl chloride and 15 ml of methylene chloride which had been preliminarily cooled in a dry ice/acetone bath. After 10 minutes, a solution of 500 mg of 2-(2-hydroxyethyl)oxy-4-(3,4-methylenedioxybenzyl)amino-6-cyanoquinazoline in 1 ml of dimethyl sulfoxide was dropped into the mixture prepared above at the same temperature and after 10 minutes, 1.4 ml of N,N-diisopropylethylamine was dropped thereinto at the same temperature. The obtained mixture was stirred at the same temperature for 10 minutes and brought to room temperature. After 20 minutes, 600 mg of ethoxycarbonylmethylenetriphenylphosphorane was added in a crystalline state to the resulting mixture to conduct a reaction for 30 minutes, followed by the addition of water. The obtained mixture was extracted with ethyl acetate and the extract was purified by silica gel column chromatography using an ethyl acetate/benzene mixture to give 400 mg of 2-(3-ethoxycarbonyl-2-propenyl)oxy-4-(3,4-methylenedioxybenzyl)amino-6-cyanoquinazoline (cis/trans mixture).

Workup

  1. temperaturehad been preliminarily cooled in a dry ice/acetone bath
  2. customprepared above at the same temperature and after 10 minutes
  3. custombrought to room temperature
  4. waitAfter 20 minutes
  5. customa reaction for 30 minutes
  6. extractionThe obtained mixture was extracted with ethyl acetate
  7. customthe extract was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5c73cd5def80458a9ec507b83a07ffea
Source dataset
uspto-grants-1996_11
Patent number
US05576322

Reaction notes

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