4-Methylmorpholine → HCID 54456794, compound

HRID 482104Notes

Reaction equation

HRID 482104 reaction equation
[CH2:1]([C:8]1[CH:14]=[CH:13][C:11]([OH:12])=[CH:10][C:9]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl>[OH:15][C:9]1[CH:10]=[C:11]([O:12][S:30]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[Cl:23])(=[O:32])=[O:31])[CH:13]=[CH:14][C:8]=1[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 79724-Methylmorpholine2×HCID 752941,3-Benzenediol, 4-(phenylmethyl)-HCID 761872-Chlorobenzenesulfonyl chloride

Product 1

HCID 54456794HCID 54456794, compoundYield 25.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C. to a solution of 708 mg (3.54 mmol) of 4-benzylresorcinol in 20 mL of methylene chloride at 0° C. was added 410 μL (3.72 mmol) of N-methylmorpholine followed by 740 mg (3.51 mmol) of 2-chlorobenzenesulfonyl chloride. The reaction mixture was warmed to ambient temperature and stirred for 30 min. An additional 400 μL of N-methylmorpholine was added and the reaction mixture was stirred for another 60 min. The reaction mixture was quenched with 1N HCl, extracted into ether, washed with saturated NaHCO3, dried (MgSO4), and purified by flash chromatography (methylene chloride) to give 336.5 mg (25%) of the title compound as a colorless oil. 1H-NMR (300 MHz, CDCl3) δ 7.95 (dd, 1H, J=1, 8 Hz), 7.55-7.63 (m, 2H), 7.34-7.40 (m, 1H), 7.1-7.3 (m, 5H), 6.98 (d, 1H), 6.61-6.65 (m, 2H), 4.95 (s, 1H), and 3.91 (s, 2H). Mass spectrum (MALDI-TOF; gentisic acid matrix) calcd. for C19H15ClO4S: 375.0 (M+H), 397.0 (M+Na). Found: 373.6, 396.7.

Workup

  1. stirringthe reaction mixture was stirred for another 60 min
  2. customThe reaction mixture was quenched with 1N HCl
  3. extractionextracted into ether
  4. washwashed with saturated NaHCO3
  5. dry with materialdried (MgSO4)
  6. custompurified by flash chromatography (methylene chloride)

Sources & evidence

ORD record
ord-552b45f3eaf341af82534fe6ca187307
Source dataset
uspto-grants-1998_08
Patent number
US05792769

Reaction notes

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