Formic Acid → HCID 22760942, compound

HRID 1703978Notes

Reaction equation

HRID 1703978 reaction equation
[CH3:1][NH:2][CH3:3].C(O)=O.O=[C:8]1[CH2:27][CH2:26][C:11]2[C:12]3[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:13]=3[O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:10]=2[CH2:9]1.O>CN(C)C=O>[CH3:1][N:2]([CH3:3])[CH:8]1[CH2:27][CH2:26][C:11]2[C:12]3[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:13]=3[O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:10]=2[CH2:9]1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 674DimethylamineHCID 962WaterHCID 22760974HCID 22760974, compound

Product 1

HCID 22760942HCID 22760942, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 10 ml of dimethylamine and 3.1 ml of 98% formic acid at -10° C. a solution of 11.5 g of 2-keto-6-chloro-1,2,3,4-tetrahydro-tribenzo(b,d,f)-oxepine in 30 ml of dimethylformamide are added dropwise. The mixture is refluxed for 10 hours. After cooling, the mixture is poured into water and extracted into ether. The ether layer is then washed with 300 ml of 2 N HCl. The acidic water layer is made alkaline with 2 N NaOH, after which the alkaline aqueous solution is extracted with ether once more. The ether layers are collected, dried and then evaporated. The oil obtained crystallizes as maleate: melting point 171° C.

Workup

  1. additionare added dropwise
  2. temperatureThe mixture is refluxed for 10 hours
  3. temperatureAfter cooling
  4. extractionextracted into ether
  5. washThe ether layer is then washed with 300 ml of 2 N HCl
  6. extractionafter which the alkaline aqueous solution is extracted with ether once more
  7. customThe ether layers are collected
  8. customdried
  9. customevaporated
  10. customThe oil obtained
  11. customcrystallizes as maleate

Sources & evidence

ORD record
ord-046975c06b254b54abaa8b9268f7920e
Source dataset
uspto-grants-1978_11
Patent number
US04125718

Reaction notes

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