Hydrochloric Acid → 1,2-Dihydro-N-(2,4-difluorophenyl)-1-oxopyrrolo[3,2,1-kl]phenothiazine-2-carboxamide

HRID 54924Notes

Reaction equation

HRID 54924 reaction equation
[H-].[Na+].[C:3]1(=O)C2[C:7]([S:8][C:9]3[C:14](N=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:6][CH:5]=[CH:4]1.[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[N:26]=[C:27]=[O:28].Cl.[CH3:30][N:31]([CH:33]=[O:34])[CH3:32]>>[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[NH:26][C:27]([CH:14]1[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]3[S:8][C:7]4[CH:6]=[CH:5][CH:4]=[CH:3][C:32]=4[N:31]([C:30]=23)[C:33]1=[O:34])=[O:28]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 5932582,4-Difluorophenyl isocyanateHCID 12998954Phenothiazine-1-one

Product 1

HCID 144599751,2-Dihydro-N-(2,4-difluorophenyl)-1-oxopyrrolo[3,2,1-kl]phenothiazine-2-carboxamide

Procedure

To a suspension of sodium hydride (0.14 g) in DMF (10 ml) was added pyrrolo[3,2, -1kl]phenothiazine-1-one (0.48 g) and to the resulting solution was slowly added 2,4-difluorophenyl isocyanate (0.31 g). The reaction mixture was stirred for 12 hours and then poured onto ice water (50 ml). The resulting mixture was acidified to pH 2.0 with 6N HCl and the precipitated solid was collected and then air dried to yield the title compound (2.84 g). A sample recrystallized from methylene chloride had a m.p. of 208°-209° C.

Workup

  1. additionwas added pyrrolo[3,2
  2. additionpoured onto ice water (50 ml)
  3. customthe precipitated solid was collected
  4. customair dried

Sources & evidence

ORD record
ord-87d4a85ef58a4c068d58b770ac1551a7
Source dataset
uspto-grants-1997_04
Patent number
US05624929

Reaction notes

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