4-Chlorobenzoyl chloride → HCID 15614760, compound

HRID 1084553Notes

Reaction equation

HRID 1084553 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]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11](=[O:19])[CH:10]([OH:20])[N:9]=1.[Cl:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([N:12]2[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])=[N:9][CH:10]([O:20][C:26]([C:25]3[CH:29]=[CH:30][C:22]([Cl:21])=[CH:23][CH:24]=3)=[O:27])[C:11]2=[O:19])=[O:27])=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 85014-Chlorobenzoyl chloride2×HCID 15167814HCID 15167814, compound

Product 1

HCID 15614760HCID 15614760, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 1,3-dihydro-5-(2-fluorophenyl)-3-hydroxy-2H-1,4-benzodiazepin-2-one (610 mg, 2.25 mmole) in 25 ml of methylene chloride was treated with 4-chlorobenzoyl chloride (0.314 ml, 2.48 mmole) at room temperature. 4-Dimethylaminopyridine (303 mg, 2.48 mmole) was added and within minutes the reaction mixture became homogeneous. The reaction mixture was protected from moisture and stirred at room temperature overnight. An additional equivalent each of 4-chlorobenzoyl chloride and 4-dimethylaminopyridine were added and stirring was continued for 8 hours at 40°-45° C. The reaction mixture was diluted to 150 ml with methylene chloride and washed in succession with 10% citric acid solution (3×50 ml), saturated sodium bicarbonate solution (3×50 ml) and brine (50 ml). Rotoevaporation of the dried (MgSO4) organic phase gave a foam which on trituration with ether afforded a beige solid. Recrystallization from ethyl acetate afforded 612 mg of the title compound as a white powder in analytical purity: m.p. 198°-199° C.

Workup

  1. stirringstirring
  2. waitwas continued for 8 hours at 40°-45° C
  3. washwashed in succession with 10% citric acid solution (3×50 ml), saturated sodium bicarbonate solution (3×50 ml) and brine (50 ml)
  4. dry with materialRotoevaporation of the dried (MgSO4) organic phase
  5. customgave a foam which on trituration with ether
  6. customafforded a beige solid
  7. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-afeecaed2865408c8fa11576d9ad5901
Source dataset
uspto-grants-1991_04
Patent number
US05004741

Reaction notes

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