HCID 12421797, compound → HCID 13851171, compound

HRID 978443Notes

Reaction equation

HRID 978443 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[O:13])[CH2:8][CH2:7]1.[N:21]([C:24]1[CH:33]=[C:32]([N+:34]([O-:36])=[O:35])[CH:31]=[CH:30][C:25]=1[C:26](OC)=[O:27])=[C:22]=[S:23]>O1CCCC1>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]([CH:9]2[CH2:8][CH2:7][N:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:1]3[C:26](=[O:27])[C:25]4[C:24](=[CH:33][C:32]([N+:34]([O-:36])=[O:35])=[CH:31][CH:30]=4)[NH:21][C:22]3=[S:23])[CH2:11][CH2:10]2)=[O:13])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 12421797HCID 12421797, compoundHCID 13851170HCID 13851170, compound

Product 1

HCID 13851171HCID 13851171, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

To a stirred solution of 28 parts of [1-(4-aminobutyl)-4-piperidinyl](4-fluorophenyl)methanone in 135 parts of tetrahydrofuran was added dropwise during a 10 minutes-period a solution of 24 parts of methyl 2-isothiocyanato-4-nitrobenzoate in 180 parts of tetrahydrofuran (slightly exothermic reaction). Upon completion, stirring was continued overnight at room temperature. The solid was filtered off and crystallized from ethanol while stirring and cooling to 40° C. The product was filtered off, washed with ethanol and dried in vacuo at 80° C., yielding 30 parts (62%) of 3-[4-[4-(4-fluorobenzoyl)-1-piperidinyl]butyl]-2,3-dihydro-7-nitro-2-thioxo-4(1H)-quinazolinone; mp. 225° C. (20).

Workup

  1. customslightly exothermic reaction)
  2. filtrationThe solid was filtered off
  3. customcrystallized from ethanol
  4. stirringwhile stirring
  5. filtrationThe product was filtered off
  6. washwashed with ethanol
  7. customdried in vacuo at 80° C.

Sources & evidence

ORD record
ord-813386625f0e47f79953346f482d3473
Source dataset
uspto-grants-1987_05
Patent number
US04665075

Reaction notes

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