Acetyl chloride → HCID 20562331, compound

HRID 848540Notes

Reaction equation

HRID 848540 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([NH:19][C:20]([NH:22][CH2:23][CH2:24][OH:25])=[O:21])[CH:17]=[CH:18][C:13]=2[N:12]([CH3:26])[C:11](=[O:27])[CH2:10][N:9]=1.[C:28](Cl)(=[O:30])[CH3:29].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:28]([O:25][CH2:24][CH2:23][NH:22][C:20]([NH:19][C:16]1[CH:17]=[CH:18][C:13]2[N:12]([CH3:26])[C:11](=[O:27])[CH2:10][N:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[C:14]=2[CH:15]=1)=[O:21])(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 3058284Urea, N-(5-(2-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl)-N(sup 1)-(2-hydroxyethyl)-

Product 1

HCID 20562331HCID 20562331, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

11.1 g (0.03 M) of 1-[5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-3-(2-hydroxyethyl)urea are stirred at room temperature for 18 hours in 150 ml of acetonitrile with 3.9 ml of acetyl chloride and 9 g of powdered potassium carbonate. The mixture is concentrated on a rotary evaporator and the residue is purified on a 500 g silica gel column using methylene chloride/ethanol as the eluting agent. After crystallisation from ethyl acetate, there is obtained 2-[3-[5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]ureido]ethyl acetate which melts at 196°-198° C.

Workup

  1. concentrationThe mixture is concentrated on a rotary evaporator
  2. customthe residue is purified on a 500 g silica gel column
  3. customAfter crystallisation from ethyl acetate

Sources & evidence

ORD record
ord-62469bd849684a538fac7385de8c0622
Source dataset
uspto-grants-1981_10
Patent number
US04296031

Reaction notes

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