Chloroacetyl chloride → 4-(Chloroacetyl)-7-(4-chlorophenyl)-4.5-dihydro-6-methylpyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 1088754Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1088754
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]3[N:14]=[CH:15][C:16]([C:17]#[N:18])=[C:12]3[NH:11][CH2:10][C:9]=2[CH3:19])=[CH:4][CH:3]=1.CN(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.[Cl:36][CH2:37][C:38](Cl)=[O:39]>O1CCCC1>[Cl:36][CH2:37][C:38]([N:11]1[CH2:10][C:9]([CH3:19])=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:13]2[N:14]=[CH:15][C:16]([C:17]#[N:18])=[C:12]12)=[O:39]

Komponenten

5

Edukt 3

HCID 6577Chloroacetyl chlorideHCID 88675Proton sponge2×HCID 1361028897-(4-Chlorophenyl)-4,5-dihydro-6-methylpyrazolo[1,5-a]pyrimidine-3-carbonitrile

Produkt 1

HCID 151010894-(Chloroacetyl)-7-(4-chlorophenyl)-4.5-dihydro-6-methylpyrazolo[1,5-a]pyrimidine-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A 10 g portion of 7-(4-chlorophenyl)-4,5-dihydro-6-methylpyrazolo[1,5-a]pyrimidine-3-carbonitrile and 9 g of [1,8-bis(dimethylamino)naphthalene, N,N,N',N'-tetramethyl-1,8-naphthalenediamine] in 300 ml of dry tetrahydrofuran under nitrogen was mixed and 6 ml of chloroacetyl chloride in 70 ml of dry tetrahydrofuran was added over 15 minutes with stirring. The mixture was stirred at reflux for 5.5 hours, then at room temperature overnight and then filtered. The filtrate was concentrated to an oil. This oil was triturated with ether, the solid collected and dried, giving 10 g of the desired intermediate, mp 138°-140° C.

Aufarbeitung

  1. stirringThe mixture was stirred
  2. temperatureat reflux for 5.5 hours
  3. filtrationat room temperature overnight and then filtered
  4. concentrationThe filtrate was concentrated to an oil
  5. customThis oil was triturated with ether
  6. customthe solid collected
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-699e96818ed14b6a88ef7e38216c7c1e
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04963553

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