Hydrochloric Acid → HCID 14234265, compound

HRID 1194756Notes

Reaction equation

HRID 1194756 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1.[N:20]([O-])=O.[Na+].[ClH:24]>O>[ClH:24].[NH:1]([C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([NH:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1)[NH2:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 132861021-(4-Aminophenyl)-N-benzylmethanesulfonamideHCID 23668193Sodium Nitrite

Product 1

HCID 14234265HCID 14234265, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A thick suspension of the product of stage (b) (3.68 g) in conc. hydrochloric acid (50 ml) was stirred at -5° whilst a solution of sodium nitrite (0.9 g) in water (10 ml) was added dropwise so that temperature did not exceed 0°. Stirring was continued for 30 min. The resulting suspension was filtered to remove starting material and the filtrate added in a few portions to a solution of stannous chloride dihydrate (13.5 g) in hydrochloric acid (15 ml) at -20° and warmed to ambient temperature. The solid that separated was filtered off and recrystallised from hot methanol (100 ml) to give the title compound as white plates (0.39 g) m.p. 192°-193°. The mother liquors afforded a second crop (0.52 g).

Workup

  1. additionwas added dropwise so that temperature
  2. customdid not exceed 0°
  3. filtrationThe resulting suspension was filtered
  4. customto remove
  5. additionthe filtrate added in a few portions to a solution of stannous chloride dihydrate (13.5 g) in hydrochloric acid (15 ml) at -20°
  6. customThe solid that separated
  7. filtrationwas filtered off
  8. customrecrystallised from hot methanol (100 ml)

Sources & evidence

ORD record
ord-c180ee72505c4f44b9b7aa32ef48f8e4
Source dataset
uspto-grants-1989_03
Patent number
US04816470

Reaction notes

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