Tetrahydrofuran → 2H-Benzimidazol-2-one,6-chloro-1,3-dihydro-1-methyl-(9CI)

HRID 1710659Notes

Reaction equation

HRID 1710659 reaction equation
ClC1[CH:3]=[C:4]([NH:9][CH3:10])[C:5]([NH2:8])=[CH:6][CH:7]=1.Cl[C:12]([Cl:22])(OC(=O)OC(Cl)(Cl)Cl)Cl.C1C[O:26][CH2:25]C1>>[Cl:22][C:12]1[CH:7]=[CH:6][C:5]2[NH:8][C:25](=[O:26])[N:9]([CH3:10])[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 94429TriphosgeneHCID 121982665-Chloro-N1-Methylbenzene-1,2-diaMine

Product 1

HCID 140429442H-Benzimidazol-2-one,6-chloro-1,3-dihydro-1-methyl-(9CI)

Procedure

A mixture of 4-chloro-N2-methyl-benzene-1,2-diamine (60) (100 mg, 0.64 mmol, 1 eq), triphosgene (95 mg, 0.32 mmol, 0.5 eq), TEA (0.26 ml) in THF (2 ml) was stirred at rt for 4 hours. The reaction solution was washed with ethyl acetate and concentrated to provide 6-chloro-1-methyl-1,3-dihydro-benzoimidazol-2-one (61).

Workup

  1. washThe reaction solution was washed with ethyl acetate
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d5378c45a38c4c07b141e6111b18a193
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

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