Pyridine → HCID 24752077, compound

HRID 252244Notes

Reaction equation

HRID 252244 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][CH:4]=[C:3]([S:7](Cl)(=[O:9])=[O:8])[CH:2]=1.N1C=CC=CC=1.[O-:18][C:19]#[N:20].[Na+].Cl.[NH2:23][C:24]1[S:25][C:26]([CH3:30])=[C:27]([CH3:29])[N:28]=1>C(#N)C.C(O)(=O)C.O>[CH3:29][C:27]1[N:28]=[C:24]([NH:23][C:19]([NH:20][S:7]([C:3]2[CH:4]=[CH:5][CH:6]=[C:1]([CH3:11])[CH:2]=2)(=[O:9])=[O:8])=[O:18])[S:25][C:26]=1[CH3:30]

Participants

8

Reactant 4

HCID 1049PyridineHCID 517096Sodium CyanateHCID 27345953-Methylbenzenesulphonyl chlorideHCID 162113874,5-Dimethyl-1,3-thiazol-2-amine--hydrogen chloride (1/1)

Product 1

HCID 24752077HCID 24752077, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

m-Toluenesulfonyl chloride (0.076 ml, 0.53 mmol, 1.4 equiv.) and pyridine (0.103 ml, 1.27 mmol, 3.4 equiv.) were added to a stirred suspension of sodium cyanate (56 mg, 0.86 mmol, 2.3 equiv.) in dry acetonitrile (1 ml) and the mixture stirred at room temperature for 3 hours. 2-Amino-4,5-dimethylthiazole hydrochloride (34 mg, 0.28 mmol, 1.0 equiv.) was added and the reaction stirred for 1 hour. Water (2 ml) and acetic acid (3 drops) were added. The resulting precipitate was centrifuged for 10 minutes and the supernatant decanted. The solid washed with water (2 ml), the material centrifuged and supernatant decanted. The solid was dried under reduced pressure at 40° C. to give N-[(4,5-dimethyl-1,3-thiazol-2-yl)carbamoyl]-3-methylbenzenesulfonamide, 49 mg (55% yield). LC @UV215 nm; Rt 1.81: 93%, m/z (ES+): 326 (MH+), 651 (2 MH+); δH(400 MHz; d4-methanol) 7.54-7.98 (4H, m), 2.57 (3H, s), 2.31 (3H, s), 2.27 (3H, s).

Workup

  1. stirringthe reaction stirred for 1 hour
  2. waitThe resulting precipitate was centrifuged for 10 minutes
  3. washThe solid washed with water (2 ml)
  4. customThe solid was dried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-207d606a02e34799af541a953586ce46
Source dataset
uspto-grants-2011_01
Patent number
US07868030B2

Reaction notes

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