Sodium Carbonate → HCID 66665880, compound

HRID 221676Notes

Reaction equation

HRID 221676 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:15]O)[NH:13][C:12](=[O:14])[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.CCN(S(F)(F)[F:23])CC.C([O-])([O-])=O.[Na+].[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:15][F:23])[NH:13][C:12](=[O:14])[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 123472(Diethylamino)sulfur trifluorideHCID 666654605-(3-Bromophenyl)-5-hydroxymethylmorpholin-3-one

Product 1

HCID 66665880HCID 66665880, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 5-(3-bromo-phenyl)-5-hydroxymethyl-morpholin-3-one (2.6 g, 9.09 mmol) and 120 ml of dichloromethane was cooled to 0° C. DAST (1.26 ml) was added dropwise. The mixture was stirred overnight, poured onto 50 ml of 10% aqueous Na2CO3 solution and ice and extracted with dichloromethane. The extract was dried with sodium sulfate and evaporated. Chromatography on silica gel (EtOAc/hexane=1:1) gave the title compound in the form of a colourless solid. TLC (hexane/EtOAc=1:1): Rf=0.31; HPLC: RtH2=3.13 min; 1H-NMR (400 MHz, CD3OD): 7.71 (s, 1H), 7.56 (d, 1H), 7.52 (d, 1H), 7.38 (t, 1H), 4.77 (d, 2H), 4.20 (s, 2H), 4.11 (d, 1H), 3.95 (d, 1H); MS: 289, 291 [(M+H)+].

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe extract was dried with sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-a63893c6913748fa822f0dd0c3c7cc8d
Source dataset
uspto-grants-2012_06
Patent number
US08207164B2

Reaction notes

Loading…