Triethylamine → HCID 68153674, compound

HRID 1405398Notes

Reaction equation

HRID 1405398 reaction equation
Cl[S:2]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:15][NH:16][C:17]1[S:18][CH:19]=[CH:20][N:21]=1.C(N(CC)CC)C>ClCCCl>[CH3:15][N:16]([C:17]1[S:18][CH:19]=[CH:20][N:21]=1)[S:2]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4738388Methyl 4-(Chlorosulfonyl)benzoateHCID 11959081N-methyl-2-Thiazolamine

Product 1

HCID 68153674HCID 68153674, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
100 °C

Procedure

To methyl 4-chlorosulfonylbenzoate (4 g, 17.05 mmol), N-methylthiazol-2-amine (1.95 g, 17.05 mmol), 1,2-dichloroethane (20 mL), and triethylamine (2.38 mL, 17.05 mmol) were added and the reaction was heated at 100° C. in a pressure vessel for 20.5 hours on a heat block. The solvent was evaporated under reduced pressure. The crude compound was dissolved in dichloromethane and filtered. The filtrate was purified by silica gel chromatography utilizing a gradient of 0-30% ethyl acetate in dichloromethane to yield methyl 4-[methyl(thiazol-2-yl)sulfamoyl]benzoate (4.22 g, 79.2%). 1H NMR (400 MHz, DMSO) δ 8.16 (d, J=8.5 Hz, 2H), 7.95 (d, J=8.5 Hz, 2H), 7.46 (d, J=3.6 Hz, 1H), 7.44 (d, J=3.6 Hz, 1H), 3.89 (s, 3H), 3.39 (s, 3H). ESI-MS m/z calc. 312.0, found 313.3 (M+1)+; Retention time: 1.52 minutes (3 min run).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionThe crude compound was dissolved in dichloromethane
  3. filtrationfiltered
  4. customThe filtrate was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d13b1432d2b54e34a452e15764813768
Source dataset
uspto-grants-2014_12
Patent number
US08916565B2

Reaction notes

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