Triethylamine → HCID 59580673, compound

HRID 2199230Notes

Reaction equation

HRID 2199230 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-e9eb1cb72c754a3281714f3c8fcacf3e
Source dataset
uspto-grants-2016_06
Patent number
US09357780B2

Reaction notes

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