Pyridine → 5-Methyl-thiophene-2-carboxylic acid (4-chloro-benzothiazol-2-yl)-amide

HRID 2308465Notes

Reaction equation

HRID 2308465 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:5]=2[N:6]=1.N1C=CC=CC=1.[CH3:18][C:19]1[S:23][C:22]([C:24](Cl)=[O:25])=[CH:21][CH:20]=1>ClCCl>[Cl:11][C:7]1[C:5]2[N:6]=[C:2]([NH:1][C:24]([C:22]3[S:23][C:19]([CH3:18])=[CH:20][CH:21]=3)=[O:25])[S:3][C:4]=2[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 298722-Benzothiazolamine, 4-chloro-HCID 27600835-Methylthiophene-2-carbonyl chloride

Product 1

HCID 865849165-Methyl-thiophene-2-carboxylic acid (4-chloro-benzothiazol-2-yl)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-4-chlorobenzothiazol (92 mg, 0.50 mmol) is dissolved in dichloromethane (10 ml) and treated with pyridine (0.060 ml, 0.75 mmol) and 5-methyl-thiophene-2-carbonyl chloride (97 mg, 0.60 mmol). The reaction mixture is stirred at ambient temperature for 18 h and then evaporated to dryness. The residue is redissolved in ethyl acetate and water, the phases are separated and the organic layer extracted with brine. After dryin with sodium silfate, the solvent is removed in vacuo Flash chromatography on silica (eluent ethyl acetate/cyclohexane 1:4 affords the product as white solid.(88 mg, 57%). MS: m/e=308 (M+).

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue is redissolved in ethyl acetate
  3. customwater, the phases are separated
  4. extractionthe organic layer extracted with brine
  5. customthe solvent is removed in vacuo Flash chromatography on silica (eluent ethyl acetate/cyclohexane 1:4

Sources & evidence

ORD record
ord-46cdeee6bc294a1cb7bf8e91ccb631c5
Source dataset
uspto-grants-2004_12
Patent number
US06835732B2

Reaction notes

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