Sodium Carbonate → HCID 20516776, compound

HRID 2199037Notes

Reaction equation

HRID 2199037 reaction equation
ClC1C2C(C3C=CC=CC=3F)=NCC(=O)N(C)C=2C=C(Cl)C=1N=C=O.[Cl:26][C:27]1[C:32]2[C:33]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=3[F:46])=[N:34][CH2:35][C:36](=[O:39])[N:37]([CH3:38])[C:31]=2[CH:30]=[C:29]([Cl:47])[C:28]=1[NH:48][C:49](=[O:53])[N:50](C)[CH3:51].NC1C(Cl)=CC2N(C)C(=O)CN=C(C3C=CC=CC=3F)C=2C=1Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.CN.ClCCCl>[Cl:26][C:27]1[C:32]2[C:33]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=3[F:46])=[N:34][CH2:35][C:36](=[O:39])[N:37]([CH3:38])[C:31]=2[CH:30]=[C:29]([Cl:47])[C:28]=1[NH:48][C:49]([NH:50][CH3:51])=[O:53]

Participants

8

Reactant 4

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

Product 1

HCID 20516776HCID 20516776, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6329MethylamineSolventHCID 6342AcetonitrileSolvent

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 5 g (14.2 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 g of sodium carbonate in 34 ml of acetonitrile and 2 ml of methylamine. The mixture is stirred at room temperature for 66 hours, concentrated in vacuo and the residue is taken up in 1.5 liter of methylene chloride/ethanol (4:1). The organic phase is washed with saturated sodium chloride solution, dried and evaporated. The residue is chromatographed on 300 g of silica gel using methylene chloride/ethyl acetate (4:1) for the elution, there being obtained 1-[6,8-dichloro-5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-3-methylurea. After recrystallisation from ether, the product melts at 213°-214° C.

Workup

  1. concentrationconcentrated in vacuo
  2. washThe organic phase is washed with saturated sodium chloride solution
  3. customdried
  4. customevaporated
  5. customThe residue is chromatographed on 300 g of silica gel
  6. washfor the elution, there

Sources & evidence

ORD record
ord-f8dacd9724c743568a21aa2859ee7cd5
Source dataset
uspto-grants-1982_11
Patent number
US04361511

Reaction notes

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