Triethylamine → HCID 23507215, compound

HRID 1947597Notes

Reaction equation

HRID 1947597 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.CCN(CC)CC.[N+:14]([C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1)([O-:16])=[O:15]>C(Cl)Cl>[N+:14]([C:17]1[CH:18]=[CH:19][C:20]([C:21]([N:1]2[CH2:6][CH2:5][S:4][CH2:3][CH2:2]2)=[O:22])=[CH:24][CH:25]=1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 67164Thiomorpholine

Product 1

HCID 23507215HCID 23507215, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of thiomorpholine (2.00 mL, 20 mmol) and Et3N (5.0 mL) in CH2Cl2 (60 mL) was added drop wise a solution of 4-nitrobenzoyl chloride (3.71 g, 20 mmol) in CH2Cl2 (50 mL) at 0° C. The reaction was allowed to stir at room temperature for over night and then washed with a saturated NaHCO3 solution (2×75 mL), and water (2×75 mL). The CH2Cl2 layer was dried (Na2SO4) and filtered and concentrated. Finally dried under high vacuum to afford 5.027 g (99%) of the 4-(4-nitrobenzoyl)thiomorpholine. 1H NMR (CDCl3, 300 MHz): δ 8.28 (d, 2H, J=9.0 Hz), 7.54 (d, 2H, J=8.7 Hz), 4.04 (br s, 2H), 3.61 (br s, 2H), 2.75 (br s, 2H), 2.57 (br s, 2H); LCMS (m/z): 253 (MH+).

Workup

  1. washwashed with a saturated NaHCO3 solution (2×75 mL), and water (2×75 mL)
  2. dry with materialThe CH2Cl2 layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customFinally dried under high vacuum

Sources & evidence

ORD record
ord-fae1ac1640ee445cac2fa92919afe341
Source dataset
uspto-grants-2013_03
Patent number
US08399472B2

Reaction notes

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