Carbon Tetrachloride → HCID 67338181, compound

HRID 1260383Notes

Reaction equation

HRID 1260383 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:21])/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([OH:20])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1.C(Cl)(Cl)(Cl)Cl.CC1C=CN=C(N)C=1C.CCN(C(C)C)C(C)C.[P:45]([O-:62])([O:54][CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>CC#N>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][P:45](=[O:62])([O:54][CH2:55][C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)[O:46][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[CH:13]=2)=[O:21])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 5943Carbon TetrachlorideHCID 81531DiisopropylethylamineHCID 110078842-Amino-3,4-dimethylpyridineHCID 21904359DibenzylphosphiteHCID 45376337HCID 45376337, compound2×

Product 1

HCID 67338181HCID 67338181, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(E)-N-(3-Chloro-phenyl)-3-(3-hydroxy-4-methoxy-phenyl)-acrylamide (compound 55, 1.608 g, 5.31 mmol) was dissolved in dry CH3CN (80 ml) and CCl4 (5.13 ml, 53.1 mmol) and the resulting solution was cooled at 0° C. Dimethyl amino pyridine (65 mg, 0.53 mmol), DIPEA (2.88 ml, 22.3 mmol) and then dibenzyl phosphite (3.52 ml, 15.93 mmol) were added and the mixture was stirred at RT for 1 h. The reaction was quenched with 0.5M KH2PO4 and extracted with AcOEt. The organic layer was dried over sodium sulphate and evaporated to dryness. The crude was purified by column chromatography (eluent DCM/MeOH from 100:1 to 99:1) to give phosphoric acid dibenzyl ester 5-[(E)-2-(3-chloro-phenylcarbamoyl)-vinyl]-2-methoxy-phenyl ester (1.87 g).

Workup

  1. customThe reaction was quenched with 0.5M KH2PO4
  2. extractionextracted with AcOEt
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. customevaporated to dryness
  5. customThe crude was purified by column chromatography (eluent DCM/MeOH from 100:1 to 99:1)

Sources & evidence

ORD record
ord-c86997dd84d54e62abd9811bc1f2b8d0
Source dataset
uspto-grants-2013_06
Patent number
US08470831B2

Reaction notes

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