Carbon Tetrachloride → HCID 59791338, compound

HRID 402216Notes

Reaction equation

HRID 402216 reaction equation
O[CH2:2][CH2:3][C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:6][CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:44]>>[Cl:44][CH2:2][CH2:3][C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 59791334HCID 59791334, compound

Product 1

HCID 59791338HCID 59791338, compound

Procedure

To tert-butyl 2-{2-[4-(2-hydroxyethyl)phenoxy]-ethoxy}ethylcarbamate (0.56 g, 1.7 mmol) dissolved in 10 ml carbon tetrachloride was added triphenylphosphine bound on styrene (861 mg, 2.6 mmol of about 3 mmol/g resin). The reaction mixture was heated to reflux for 2 hours. After the required time the reaction was cooled and filtered. After drying a quantitative yield of product was isolated. 1H NMR (CDCl3) δ 7.11 (d, 2H, Ar), 6.86 (d, 2H, Ar), 4.95 (bs, exchangeable, NH), 4.08 (dd, CH2—O), 3.79 (dd, CH2—O), 3.65 (t, CH2—Cl), 3.59 (t, CH2—O), 3.32 (bm, CH2—NH), 2.99 (t, CH2—Ar), 1.70 (bs, exchangeable, OH) 1.42 (s, 9H, CH3). Mass spectrum, m/e Calcd for C17H27ClNO4+: 344.16 (100%), 346.16 (32%). Found: 344.57, 346.55.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperatureAfter the required time the reaction was cooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-0cae071506f34cc1984f9b0524b752bb
Source dataset
uspto-grants-2014_06
Patent number
US08742086B2

Reaction notes

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