Hydrochloric Acid → 3-Cyano-4-fluoro-N-(thiazol-2-yl)benzenesulfonamide

HRID 46282Notes

Reaction equation

HRID 46282 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.N1C=CC=CC=1.[C:13]([C:15]1[CH:16]=[C:17]([S:22](Cl)(=[O:24])=[O:23])[CH:18]=[CH:19][C:20]=1[F:21])#[N:14].Cl>ClCCl>[C:13]([C:15]1[CH:16]=[C:17]([S:22]([NH:1][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)(=[O:24])=[O:23])[CH:18]=[CH:19][C:20]=1[F:21])#[N:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 21552-AminothiazoleHCID 27789083-Cyano-4-fluorobenzenesulfonyl chloride

Product 1

HCID 580422683-Cyano-4-fluoro-N-(thiazol-2-yl)benzenesulfonamideYield 66.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 2-aminothiazole (12.55 g, 125.3 mmol) was added pyridine (46 ml) and dichloromethane (75 mL) and the mixture stirred to give a solution. A solution of 3-cyano-4-fluorobenzenesulfonyl chloride (25 g, 114 mmol) in dichloromethane (50 ml) was added over approx 20 minutes at room temperature. The reaction was stirred at this temperature for 2 days before decanting the supernatant and concentrating in vacuo to furnish a dark oil. 2M HCl (200 ml) was added and the mixture triturated until solidification occurred. A brick red solid was filtered off, washed with water and dried to furnish 21.5 g of the title product. 1HNMR (d6-DMSO): δ 6.9 (d, 1H), 7.3 (m, 1H), 7.6 (m, 1H), 8.15 (m, 1H), 8.3 (d, 1H), 12.9 (br s 1H). LCMS Rt=2.34 min MS m/z 284 [MH]+.

Workup

  1. customto give a solution
  2. stirringThe reaction was stirred at this temperature for 2 days
  3. custombefore decanting the supernatant and
  4. concentrationconcentrating in vacuo
  5. customto furnish a dark oil
  6. customthe mixture triturated until solidification
  7. filtrationA brick red solid was filtered off
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-9edad214163b4510a45d7125ccc1060f
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Reaction notes

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