Triethylamine → N-(5-bromothiazol-2-yl)-5-chloro-2-methoxybenzamide

HRID 538825Notes

Reaction equation

HRID 538825 reaction equation
[NH2:1][C:2]1[S:3][C:4]([Br:7])=[CH:5][N:6]=1.C(N(CC)CC)C.[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([O:25][CH3:26])=[C:20]([CH:24]=1)[C:21](Cl)=[O:22]>ClCCl.CN(C)C1C=CN=CC=1>[Br:7][C:4]1[S:3][C:2]([NH:1][C:21](=[O:22])[C:20]2[CH:24]=[C:16]([Cl:15])[CH:17]=[CH:18][C:19]=2[O:25][CH3:26])=[N:6][CH:5]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 436002-Thiazolamine, 5-bromo-HCID 123841765-Chloro-2-methoxybenzoyl chloride

Product 1

HCID 60654877N-(5-bromothiazol-2-yl)-5-chloro-2-methoxybenzamideYield 66%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-5-bromothiazole (1220 mg, 6.81 mmol) in dichloromethane (10 ml) was added triethylamine (1.235 ml, 8.86 mmol) and 4-dimethylamino pyridine (83 mg, 0.681 mmol), followed by addition of 5-chloro-2-methoxybenzoyl chloride (1397 mg, 6.81 mmol) and stirred overnight. The reaction was concentrated and water was added to the residue. The mixture was sonicated and filtered to obtain the title compound as off-white solid (1.56 g, 66%). 1H NMR (300 MHz, DMSO-D6) δ ppm 3.88 (m, 3H) 7.23 (d, J=8.81 Hz, 1H) 7.58-7.67 (m, 3H) 12.32 (s, 1H); MS (DCI/NH3) m/z 347 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated
  2. additionwater was added to the residue
  3. customThe mixture was sonicated
  4. filtrationfiltered

Sources & evidence

ORD record
ord-abc9c3b3243c4b7fa8ff1ce75926eca7
Source dataset
uspto-grants-2014_10
Patent number
US08865753B2

Reaction notes

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