4-(Chloromethyl)benzoyl chloride → 4-chloromethyl-N-(7-cyclohexyl-4-methoxy-benzothiazol-2-yl)-benzamide

HRID 1582143Notes

Reaction equation

HRID 1582143 reaction equation
[CH:1]1([C:7]2[C:15]3[S:14][C:13]([NH2:16])=[N:12][C:11]=3[C:10]([O:17][CH3:18])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(C(C)C)C(C)C)C.[Cl:28][CH2:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1>C1COCC1.ClCCl>[Cl:28][CH2:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([NH:16][C:13]2[S:14][C:15]3[C:7]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)=[CH:8][CH:9]=[C:10]([O:17][CH3:18])[C:11]=3[N:12]=2)=[O:35])=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 701364-(Chloromethyl)benzoyl chlorideHCID 81531DiisopropylethylamineHCID 227195747-Cyclohexyl-4-methoxy-benzothiazol-2-ylamine

Product 1

HCID 227195604-chloromethyl-N-(7-cyclohexyl-4-methoxy-benzothiazol-2-yl)-benzamideYield 69.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.1 g (0.38 mMol) 7-cyclohexyl-4-methoxy-benzothiazol-2-ylamine in 3 ml THF were added 0.2 ml ethyl diisopropyl amine and 0.0865 g (0.46 mMol) 4-chloromethyl-benzoyl chloride, dissolved in 1 ml of dichloro methane. The reaction mixture was stirred at room temperature for 16 h. The solvent was evaporated to dryness, the residue taken up in dichloro methane and washed with water and brine. The organic phase was dried over sodium sulfate and evaporated to dryness in vacuo. The residue was triturated in ethyl ether, filtered and dried to yield 0.11 g (68%) of 4-chloromethyl-N-(7-cyclohexyl-4-methoxy-benzothiazol-2-yl)-benzamide as a light yellow foam. ES-MS m/e (%): 415 ([M+H]+, 100).

Workup

  1. customThe solvent was evaporated to dryness
  2. washwashed with water and brine
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated to dryness in vacuo
  5. customThe residue was triturated in ethyl ether
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-f59081e1aaba44c382626c793bcc5716
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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