Triethylamine → HCID 59580673, compound

HRID 1470443Notes

Reaction equation

HRID 1470443 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[S:12][C:11]([Cl:13])=[N:10][C:9]=1[Cl:14])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:23][S:24][CH2:25][CH2:26][C:27](Cl)=[O:28]>ClC(Cl)C.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6](=[O:15])[N:7]([C:8]1[S:12][C:11]([Cl:13])=[N:10][C:9]=1[Cl:14])[C:27](=[O:28])[CH2:26][CH2:25][S:24][CH3:23])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 129214403-(Methylthio)propionyl ChlorideHCID 59580961HCID 59580961, compound

Product 1

HCID 59580673HCID 59580673, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of (2,4-dichloro-thiazol-5-yl)-carbamic acid tert-butyl ester (1.0 g, 3.7 mmol) in dichloroethane (20 mL) stirring at room temperature was added triethylamine (935 mg, 9.25 mmol), followed by dropwise addition of methylsulfanyl-propionyl chloride (776 mg, 5.6 mmol) and the mixture was stirred for 5 min before DMAP (45 mg, 0.37 mmol) was added. The mixture was stirred at 75° C. for 4 h. The reaction mixture was cooled, quenched with H2O (30 mL). The organic layer was separated and the aqueous layer extracted with dichloromethane (20 mL). The combined organic layer was dried over Na2SO4 and purified by silica gel chromatography (0 to 100% ethyl acetate/hexanes) to give product as a colorless oil (1.11 g, 81%): 1H NMR (300 MHz, CDCl3) δ 3.32 (t, J=7.3 Hz, 2H), 2.83 (t, J=7.3 Hz, 2H), 2.16 (s, 3H), 1.46 (s, 9H); ESIMS m/z 371.2 (M+1).

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled
  3. customquenched with H2O (30 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer extracted with dichloromethane (20 mL)
  6. dry with materialThe combined organic layer was dried over Na2SO4
  7. custompurified by silica gel chromatography (0 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8f6d58ad93d84649ad738e5a8737f4eb
Source dataset
uspto-grants-2015_04
Patent number
US09006446B2

Reaction notes

Loading…