Thionyl Chloride → HCID 23295002, compound

HRID 1955265Notes

Reaction equation

HRID 1955265 reaction equation
[C:1]1([C:7]2([C:11]([OH:13])=[O:12])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=S(Cl)[Cl:16].[CH:18]([N:21]([CH:25](O)[CH3:26])[CH:22](C)[CH3:23])(C)[CH3:19]>>[ClH:16].[C:1]1([C:7]2([C:11]([O:13][CH2:19][CH2:18][N:21]([CH2:25][CH3:26])[CH2:22][CH3:23])=[O:12])[CH2:8][CH2:9][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 2771711-Phenylcyclobutanecarboxylic acidHCID 22348659Diisopropylaminoethanol

Product 1

HCID 23295002HCID 23295002, compound

Conditions

Temperature
80 °C

Procedure

1-Phenylcyclobutanecarboxylic acid (1.9 mmol) was refluxed with SOCl2 (5 mL). After 0.5 h, the reaction mixture was evaporated and the residue dissolved in toluene. Diisopropylaminoethanol (3.8 mmol) was added and the mixture was heated at 80° C. for 1.5 h. The reaction mixture was filtered and chromatographed on silica gel using toluene-Et3N 95:5 as eluent. The yield was 1.3 g (73%); mp 137-139° C.; 1H NMR (D2O) δ 1.25 (t, 6H), 1.92-2.01 (m, 1H), 2.07-2.16 (m, 1H), 2.64 (m, 2H), 2.89 (m, 2H), 3.11 (q, 4H), 3.50 (t, 2H), 4.48 (t, 2H), 7.44 (m, 1H), 7.48 (m, 2H), 7.53 (m, 2H). Anal. (C17H25NO2.HCl) C, H, N.

Workup

  1. customthe reaction mixture was evaporated
  2. dissolutionthe residue dissolved in toluene
  3. filtrationThe reaction mixture was filtered
  4. customchromatographed on silica gel

Sources & evidence

ORD record
ord-18f4d0e48b7145678c6c6cd10f086ed9
Source dataset
uspto-grants-2000_09
Patent number
US06124354

Reaction notes

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