Trifluoroacetic acid → Trifluoroacetic acid

HRID 852947Notes

Reaction equation

HRID 852947 reaction equation
[CH3:1][NH:2][C:3]1[C:4]([NH2:12])=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1.[CH:13](OC)(OC)OC.[C:20]([OH:26])([C:22]([F:25])([F:24])[F:23])=[O:21]>C(Cl)Cl>[CH3:1][N:2]1[C:3]2[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=2[N:12]=[CH:13]1.[C:20]([OH:26])([C:22]([F:25])([F:24])[F:23])=[O:21]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 9005Trimethyl orthoformateHCID 34200251-N-methyl-4-nitrobenzene-1,2-diamine

Product 2

HCID 6422Trifluoroacetic acidYield 192.6%HCID 961731-methyl-5-nitro-1H-benzo[d]imidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of diamine 248 (1.14 g, 6.80 mmol) in CH2Cl2 (10 mL) was added trimethyl orthoformate (5 mL, 46 mmol, 6.7 eq) (or any other acylating agent of choice, 6 eq) followed by TFA (0.43 mL, 5.6 mmol, 0.8 eq) and the mixture was stirred at room temperature for 2 h. Precipitate was collected by filtration, washed with CH2Cl2 and dried to afford the title compound 249 as TFA salt (1.23 g, 62% yield). 1H NMR: (CDCl3) δ (ppm): 8.57 (d, J=1.8 Hz, 1H), 8.20 (dd, J=1.8, 9.2 Hz, 1H), 8.18 (s, 1H), 7.54 (d, J=9.2 Hz, 1H), 3.94 (s, 3H). LRMS: (calc.) 177.2; (obt.) 178.1 (MH)+.

Workup

  1. filtrationPrecipitate was collected by filtration
  2. washwashed with CH2Cl2
  3. customdried

Sources & evidence

ORD record
ord-cf29446035244d0ba1713bd35cfba878
Source dataset
uspto-grants-2007_08
Patent number
US07253204B2

Reaction notes

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