Dimethylformamide → HCID 70101090, compound

HRID 1955593Notes

Reaction equation

HRID 1955593 reaction equation
[NH2:1][CH:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[NH:4][C:3]1=[O:14].C(CCC[NH:22][C:23]([O:25][CH2:26][C:27]1[CH:28]=[C:29]([N:33]=[C:34]=[O:35])[CH:30]=[CH:31][CH:32]=1)=[O:24])(OC)=O.CN(C)[CH:38]=[O:39]>>[C:26]([CH2:27][CH2:32][CH2:31][CH:26]([O:25][C:23](=[O:24])[NH2:22])[C:27]1[CH:28]=[C:29]([NH:33][C:34](=[O:35])[NH:1][CH:2]2[C:8](=[O:9])[NH:7][C:6]3[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=3[NH:4][C:3]2=[O:14])[CH:30]=[CH:31][CH:32]=1)([O:39][CH3:38])=[O:25]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 19070806HCID 19070806, compoundHCID 219558063-amino-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Product 1

HCID 70101090HCID 70101090, compoundYield 100%

Procedure

A mixture of 3-amino-1H-1,5-benzodiazepine-2,4(3H,5H)-dione (1.91 g, 10.0 mmol) and 3-(3-(carbomethoxy)propylcarbamoyloxymethyl)phenylisocyanate (3.507 g, 12.0 mmol) in dimethylformamide (19 ml) is stirred for 1 hr at room temperature. To the residue obtained by concentrating the reaction mixture under reduced pressure is added methylene chloride (300 ml) and methanol (100 ml), and the mixture is stirred for 30 min at room temperature. The reaction mixture is filtered through a silica gel (50 g) layer to obtain Compound 6 (4.822 g, 100%) as colorless crude crystals. M.p. =151°-155° C.

Workup

  1. customTo the residue obtained
  2. concentrationby concentrating the reaction mixture under reduced pressure
  3. additionis added methylene chloride (300 ml) and methanol (100 ml)
  4. stirringthe mixture is stirred for 30 min at room temperature
  5. filtrationThe reaction mixture is filtered through a silica gel (50 g) layer

Sources & evidence

ORD record
ord-a26a8af89fce4eaf93cc97f73bddba01
Source dataset
uspto-grants-1998_07
Patent number
US05776929

Reaction notes

Loading…