Sodium Carbonate → HCID 20516778, compound

HRID 2199035Notes

Reaction equation

HRID 2199035 reaction equation
[Cl:1][C:2]1[C:7]2[C:8]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[F:21])=[N:9][CH2:10][C:11](=[O:14])[N:12]([CH3:13])[C:6]=2[CH:5]=[C:4]([Cl:22])[C:3]=1[N:23]=[C:24]=[O:25].ClC1[C:32]2[C:33]([C:40]3C=CC=CC=3F)=[N:34][CH2:35][C:36](=O)[N:37](C)[C:31]=2C=C(Cl)C=1NC(=O)N(C)C.NC1C(Cl)=CC2N(C)C(=[O:66])CN=C(C3C=CC=CC=3F)C=2C=1Cl.C(=O)([O-])[O-].[Na+].[Na+]>OCCN1CCNCC1.C(Cl)Cl.ClCCCl>[Cl:1][C:2]1[C:7]2[C:8]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[F:21])=[N:9][CH2:10][C:11](=[O:14])[N:12]([CH3:13])[C:6]=2[CH:5]=[C:4]([Cl:22])[C:3]=1[NH:23][C:24]([N:34]1[CH2:35][CH2:36][N:37]([CH2:31][CH2:32][OH:66])[CH2:40][CH2:33]1)=[O:25]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 20516774HCID 20516774, compoundHCID 20516775HCID 20516775, compoundHCID 20516784HCID 20516784, compound

Product 1

HCID 20516778HCID 20516778, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolventHCID 76771-(2-Hydroxyethyl)piperazineSolvent

Procedure

A 1,2-dichloroethane solution of [6,8-dichloro-5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]isocyanate, prepared in analogy to the procedure described in paragraph (a) of Example 4 from 6 g (17.1 mmol) of 7-amino-6,8-dichloro-5-(o-fluorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one, is treated with a suspension of 6.11 g of sodium carbonate in 6.3 ml of N-(2-hydroxyethyl)piperazine and 40 ml of methylene chloride. The mixture is stirred at room temperature for 138 hours and concentrated in vacuo. The residue is taken up in 1.5 liter of methylene chloride/ethanol (4:1), the solution is washed with 300 ml of water, dried over magnesium sulphate and evaporated. The residue is chromatographed on 250 g of silica gel using chloroform for the elution, there being obtained N-[6,8-dichloro-5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-4-(2-hydroxyethyl)-1-piperazinecarboxamide. After recrystallisation from methylene chloride/hexane, the product melts at 232°-233° C.

Workup

  1. concentrationconcentrated in vacuo
  2. washthe solution is washed with 300 ml of water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue is chromatographed on 250 g of silica gel
  6. washfor the elution, there

Sources & evidence

ORD record
ord-572fdcf0e14746419d6fd2fbf3af4b92
Source dataset
uspto-grants-1982_11
Patent number
US04361511

Reaction notes

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