Formaldehyde → HCID 10453028, compound

HRID 898623Notes

Reaction equation

HRID 898623 reaction equation
[CH2:1]=O.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][NH:28][CH3:29])=[CH:23][CH:22]=3)=[O:19])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1>C(O)=O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13](/[CH:16]=[CH:17]/[C:18]([NH:20][C:21]3[CH:22]=[CH:23][C:24]([CH2:27][N:28]([CH3:1])[CH3:29])=[CH:25][CH:26]=3)=[O:19])=[CH:14][CH:15]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 59691708HCID 59691708, compound

Product 1

HCID 10453028HCID 10453028, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
90 °C

Procedure

1.00 mL formaldehyde (37% in water) was added at 0° C. to a solution of 0.100 g (0.280 mmol) (E)-3-(4′-chloro-biphenyl-4-yl)-N-(4-methylaminomethyl-phenyl)-acrylamide (Example 180) in 1 mL formic acid and the mixture was stirred for 1 h at RT and 2 h at 90° C. The reaction mixture was poured onto ice water and the aqueous phase was exhaustively extracted with EtOAc. The combined org. phases were dried over sodium sulphate, evaporated down i. vac. and the residue stirred with ether. The precipitate was filtered off, washed with ether and dried i. vac. at 100° C.

Workup

  1. additionThe reaction mixture was poured onto ice water
  2. extractionthe aqueous phase was exhaustively extracted with EtOAc
  3. dry with materialphases were dried over sodium sulphate
  4. customevaporated down i
  5. stirringand the residue stirred with ether
  6. filtrationThe precipitate was filtered off
  7. washwashed with ether
  8. customdried i
  9. customat 100° C.

Sources & evidence

ORD record
ord-96a465cc2cf74ac9803586015cdee3ee
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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