Pyridine → N-(5-bromothiazol-2-ylcarbamoyl)-5-methylbenzo[b]thiophene-2-sulfonamide

HRID 1009001Notes

Reaction equation

HRID 1009001 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][C:5]2[S:6][C:7]([S:9](Cl)(=[O:11])=[O:10])=[CH:8][C:4]=2[CH:3]=1.[O-:15][C:16]#[N:17].[Na+].N1C=CC=CC=1.Br.[NH2:26][C:27]1[S:28][C:29]([Br:32])=[CH:30][N:31]=1>C(#N)C>[Br:32][C:29]1[S:28][C:27]([NH:26][C:16]([NH:17][S:9]([C:7]2[S:6][C:5]3[CH:13]=[CH:14][C:2]([CH3:1])=[CH:3][C:4]=3[CH:8]=2)(=[O:11])=[O:10])=[O:15])=[N:31][CH:30]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 517096Sodium CyanateHCID 27238485-Bromothiazol-2-amine monohydrobromideHCID 27947715-Methyl-1-benzothiophene-2-sulfonyl chloride

Product 1

HCID 42634696N-(5-bromothiazol-2-ylcarbamoyl)-5-methylbenzo[b]thiophene-2-sulfonamideYield 78.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 5-methyl-benzo[b]thiophenesulfonyl chloride (Maybridge, CAS: 90273-30-6, 0.37 g) in acetonitrile (5.0 mL) were added sodium cyanate (0.163 g) in one portion and pyridine (0.60 mL). The reaction mixture was stirred at rt for 3 h, then 2-amino-5-bromothiazole hydrobromide (0.286 g) was added in one portion. The mixture was stirred at rt for 4 h and quenched with 70% acetic acid (2.4 mL) and water (4.0 mL). The suspension was filtered, washed with waterlethanol and water, dried over P2O5 under high vacuum to obtain the desired compound (0.372 g) as a creamy solid. MS (ISN): m/e 430.1, 432.0 (M−H)−

Workup

  1. stirringThe mixture was stirred at rt for 4 h
  2. customquenched with 70% acetic acid (2.4 mL) and water (4.0 mL)
  3. filtrationThe suspension was filtered
  4. washwashed with waterlethanol and water
  5. dry with materialdried over P2O5 under high vacuum

Sources & evidence

ORD record
ord-79accb4e2e0c4db8b83d899b07c47d1d
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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