Triethylamine → HCID 53240570, compound

HRID 1475993Notes

Reaction equation

HRID 1475993 reaction equation
[C:1]([O:4][NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([CH3:18])(=[O:17])=[O:16])(=[O:8])=[O:7])(=[O:3])[CH3:2].C(N(CC)CC)C.Cl[C:27]([O:29][CH2:30][CH3:31])=[O:28]>ClCCl>[C:1]([O:4][N:5]([S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([CH3:18])(=[O:16])=[O:17])(=[O:8])=[O:7])[C:27](=[O:28])[O:29][CH2:30][CH3:31])(=[O:3])[CH3:2].[C:1]([O:4][NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([CH3:18])(=[O:16])=[O:17])(=[O:8])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 53240570HCID 53240570, compound

Product 2

HCID 53240570HCID 53240570, compoundHCID 53240985HCID 53240985, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl (acetyloxy){[2-(methylsulfonyl)phenyl]sulfonyl}-carbamate (48) is prepared according to Scheme 3. To a stirred solution of N-(acetyloxy)-2-(methylsulfonyl)benzene-sulfonamide (0.085 g, 0.29 mmol) in dichloromethane (5 ml) is added triethylamine (50 μl, 0.35 mmol) and ethyl chloroformate (30 μl, 0.32 mmol). The reaction mixture is stirred for 3 hours before quenching with water (1 ml). The organics are separated and dried over sodium sulfate, filtered and concentrated in vacuo to yield the title compound which is purified by silica column chromatography, eluting with 40% ethyl acetate: heptane. (60 mg, 57%), 1H NMR (250 MHz, CHLOROFORM-d) δ ppm 8.47-8.58 (1H, m), 8.34-8.45 (1H, m), 7.82-7.94 (2H, m), 4.25 (2H, q, 7.2 Hz), 3.42 (3H, s), 2.31 (3H, s), 1.25 (3H, t, 7.2 Hz).

Workup

  1. custombefore quenching with water (1 ml)
  2. customThe organics are separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-80d7011233e046ea817ce71f98806b18
Source dataset
uspto-grants-2015_04
Patent number
US09018411B2

Reaction notes

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