2,2'-Dithiodibenzoyl chloride → 2,2'-Dithiobis[N-(5-bromo-2-pyrimidinyl)benzamide]

HRID 583511Notes

Reaction equation

HRID 583511 reaction equation
[C:1](Cl)(=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][S:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12](Cl)=[O:13].[NH2:21][C:22]1[N:27]=[CH:26][C:25]([Br:28])=[CH:24][N:23]=1>ClCCl.N1C=CC=CC=1>[Br:28][C:25]1[CH:24]=[N:23][C:22]([NH:21][C:1](=[O:19])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8][S:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([NH:21][C:22]2[N:27]=[CH:26][C:25]([Br:28])=[CH:24][N:23]=2)=[O:13])=[N:27][CH:26]=1

Participants

5

Reactant 2

HCID 881642,2'-Dithiodibenzoyl chlorideHCID 2313102-Amino-5-bromopyrimidine

Product 1

HCID 189352872,2'-Dithiobis[N-(5-bromo-2-pyrimidinyl)benzamide]Yield 11.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane and 2-amino-5-bromopyrimidine (2.03 g, 11.7 mmol) in 16 mL of pyridine. The crude product was triturated with a hot mixture of ethyl acetate and ethanol, filtered, and recrystallized first from DMF, then from acetonitrile-DMF to yield 0.40 g of the title compound, mp 249-253° C.

Workup

  1. customThis compound was prepared
  2. customThe crude product was triturated with a hot mixture of ethyl acetate and ethanol
  3. filtrationfiltered
  4. customrecrystallized first from DMF

Sources & evidence

ORD record
ord-807ff337a5da4f14a33b38fec6348d5e
Source dataset
uspto-grants-1999_07
Patent number
US05929114

Reaction notes

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