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

HRID 1088754Notes

Reaction equation

HRID 1088754 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-699e96818ed14b6a88ef7e38216c7c1e
Source dataset
uspto-grants-1990_10
Patent number
US04963553

Reaction notes

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