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

HRID 2250699Notes

Reaction equation

HRID 2250699 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-dd1486de7a6e4452806fef172253895e
Source dataset
uspto-grants-2008_01
Patent number
US07317007B2

Reaction notes

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