Hydrochloric Acid → HCID 178424090, compound

HRID 2422821Notes

Reaction equation

HRID 2422821 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=2[C:19]#[N:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N-:21]=[N+:22]=[N-:23].[Na+].[Cl-].[NH4+].Cl>CN(C=O)C>[NH:21]1[C:19]([C:13]2[CH:14]=[CH:15][C:16]([CH3:18])=[CH:17][C:12]=2[NH:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])=[N:20][N:23]=[N:22]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 24961447HCID 24961447, compound

Product 1

HCID 178424090HCID 178424090, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was synthesized by reacting 2-{[(4-fluorophenyl)sulfonyl]amino}-4-methylbenzenecarbonitrile (13) (0.1 g, 0.34 mmol), sodium azide (0.09 g, 1.37 mmol), and ammonium chloride (0.74 g, 1.37 mmol) in 3 mL of DMF at 120° C. for 20 h.23 Reaction mixture was poured into ice cold water (30 mL) and acidified with dilute HCl solution. The white precipitate obtained on acidification was extracted with ethyl acetate. The organic layer was washed (H2O) dried (Na2SO4) and concentrated to give crude product (0.1 g), which was purified by FCC (silica gel, CH2Cl2, MeOH, CH3COOH, 10:2:0.1, v/v/v) to give 13 as white solid (0.086 g, 74.9%) mp: 152-154° C.; IR (CHCl3) 3136, 1457, 1376, 1348, 1165, 1153 cm−1; 1H NMR (500 MHz, DMSOD6) δ 2.36 (s, 3H, CH3), 7.17-7.81 (m, 6H, aromatic) and 10.81 (br, 1H, NH). HRMS calcd 356.0587 (C14H12FN5O2S.Na+), found 356.0587.

Workup

  1. customat 120° C.
  2. customfor 20 h
  3. custom23 Reaction mixture
  4. customThe white precipitate obtained on acidification
  5. extractionwas extracted with ethyl acetate
  6. washThe organic layer was washed (H2O)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customto give crude product (0.1 g), which

Sources & evidence

ORD record
ord-82c0cbd1bd5a489096e8d8f17784ccad
Source dataset
uspto-grants-2011_06
Patent number
US07960435B2

Reaction notes

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