Tert-Butylamine → Urea, N-(1,1-dimethylethyl)-N(sup 1)-(5-(2-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl)-

HRID 1155106Notes

Reaction equation

HRID 1155106 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:6]=2[CH:21]=1.[C:22]([NH2:26])([CH3:25])([CH3:24])[CH3:23].[CH2:27](Cl)Cl.[OH2:30]>>[C:22]([NH:26][C:27]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:6]=2[CH:21]=1)=[O:30])([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 3

HCID 6385Tert-ButylamineHCID 922947-AminoflunitrazepamHCID 21908982Water methylene chloride

Product 1

HCID 3058283Urea, N-(1,1-dimethylethyl)-N(sup 1)-(5-(2-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl)-

Procedure

A dichloroethane solution of [5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]isocyanate, obtained as described in paragraph (a) of Example 1 from 4.2 g (0.015 M) of 7-amino-5-(o-fluorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one, is treated with excess tert.butylamine. After concentration of the mixture, the residue is taken up in methylene chloride/water and the methylene chloride solution is washed several times with water. After drying the organic phase over sodium sulphate, the sodium sulphate is filtered off and the methylene chloride is evaporated off. The residue is purified on a silica gel column (150 g of SiO2) using 40% ethyl acetate in methylene chloride as the eluting agent and crystallised from ethanol/petroleum ether. There is obtained 1-tert.butyl-3-[5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]urea which melts at 210° C. with decomposition.

Workup

  1. washthe methylene chloride solution is washed several times with water
  2. dry with materialAfter drying the organic phase over sodium sulphate
  3. filtrationthe sodium sulphate is filtered off
  4. customthe methylene chloride is evaporated off
  5. customThe residue is purified on a silica gel column (150 g of SiO2)
  6. customcrystallised from ethanol/petroleum ether

Sources & evidence

ORD record
ord-78fb0569546444d7a35ff6cd9aafcc0f
Source dataset
uspto-grants-1981_11
Patent number
US04299767

Reaction notes

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