Ethanol → HCID 21467465, compound

HRID 1939303Notes

Reaction equation

HRID 1939303 reaction equation
[F:1][CH:2]([F:28])[C:3]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:7]=3[C:6]=2[N:5]([C:18]2[CH:23]=[CH:22][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)[N:4]=1.[Cl:29]N1C(=O)CCC1=O.C(O)C>C(Cl)(Cl)Cl>[Cl:29][C:12]1[C:8]2=[CH:9][CH:10]=[C:11]3[C:6]([N:5]([C:18]4[CH:23]=[CH:22][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:20][CH:19]=4)[N:4]=[C:3]3[CH:2]([F:1])[F:28])=[C:7]2[CH:15]=[CH:14][C:13]=1[O:16][CH3:17]

Participants

5

Reactant 3

HCID 702EthanolHCID 31398Chlorosuccinimide2×HCID 22315385HCID 22315385, compound

Product 1

HCID 21467465HCID 21467465, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

4-[3-(Difluoromethyl)-4,5-dihydro-7-methoxy-1H-benz[g]indazol-1-yl]benzenesulfonamide (1.0 g, 1.23 mmol) from Step 2 was suspended in chloroform (100 ml), and N-chlorosuccinimide (NCS) (329 mg, 1.23 mmol) was added. The reaction was heated to 50° C. for 16 hours. At this point, ethanol (20 ml) was added to dissolve the suspended reagents. The reaction was again heated to 50° C. for 24 hours. At this time, an additional equivalent of NCS (329 mg) was added, and the reaction was heated to 50° C. for an additional 4 days. Upon cooling, a precipitate which had formed was collected. This solid was pure 4-[6-chloro-3-(difluoromethyl)-7-methoxy-1H-benz[g]indazol-1-yl]benzenesulfonamide (350 mg, 65%): 1H NMR (acetone d6) δ=4.0 (s, 3H), 7.2 (t, 1H, j=54.0 Hz), 7.3 (d, 1H j=9.3 Hz), 7.6 (d, 1H j=9.3 Hz), 7.9 (d, 2H j=8.7 Hz), 8.0 (d, 1H j=9.3 Hz), 8.1 (d, 1H j=9.3 Hz), 8.2 (d, 2H j=8.7 Hz); 19F NMR (acetone d6) δ-113.5 ppm (d, 2F).

Workup

  1. dissolutionto dissolve the suspended reagents
  2. temperatureThe reaction was again heated to 50° C. for 24 hours
  3. temperaturethe reaction was heated to 50° C. for an additional 4 days
  4. temperatureUpon cooling
  5. customa precipitate which had formed
  6. customwas collected

Sources & evidence

ORD record
ord-23f47048a9e34dba805c04845a42af12
Source dataset
uspto-grants-1997_12
Patent number
US05696143

Reaction notes

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