Sodium Carbonate → HCID 20516777, compound

HRID 2199036Notes

Reaction equation

HRID 2199036 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]2C(C3C=CC=CC=3F)=[N:34][CH2:35][C:36](=O)[N:37]([CH3:38])[C:31]=2C=C(Cl)C=1NC(=O)N(C)C.NC1C(Cl)=CC2N(C)[C:63](=[O:66])CN=C(C3C=CC=CC=3F)C=2C=1Cl.C(=O)([O-])[O-].[Na+].[Na+]>NCCN1CCOCC1.ClC(Cl)C.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]([NH:34][CH2:35][CH2:36][N:37]1[CH2:31][CH2:32][O:66][CH2:63][CH2:38]1)=[O:25]

Participants

8

Reactant 4

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

Product 1

HCID 20516777HCID 20516777, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 63651,1-DichloroethaneSolventHCID 4082852-MorpholinoethylamineSolvent

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 5.5 g (15.62 mmol) of 7-amino-6,8-dichloro-5-(o-fluorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one, is treated at room temperature all at once with a suspension of 6.11 g of sodium carbonate in 6.1 ml of N-(2-aminoethyl)morpholine and 40 ml of dichloroethane and the mixture is stirred for 114 hours. The mixture is extracted with methylene chloride/ethanol (4:1), the organic phase is washed with water, dried and evaporated. The residue is chromatographed on 250 g of silica gel using chloroform 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-(2-morpholinoethyl)urea. After recrystallisation from ether, the product melts at 174°-176° C.

Workup

  1. additionis treated at room temperature all at
  2. extractionThe mixture is extracted with methylene chloride/ethanol (4:1)
  3. washthe organic phase is washed with water
  4. customdried
  5. customevaporated
  6. customThe residue is chromatographed on 250 g of silica gel
  7. washfor the elution, there

Sources & evidence

ORD record
ord-cad937b0f1da4dc4832ae8df1e09eae3
Source dataset
uspto-grants-1982_11
Patent number
US04361511

Reaction notes

Loading…