Formic Acid → HCID 21421756, compound

HRID 1730042Notes

Reaction equation

HRID 1730042 reaction equation
[C:1]1([CH:7]([NH:9][CH2:10][C:11]#[N:12])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC1C=CC=CC=1C.[CH:21](O)=[O:22]>O>[C:11]([CH2:10][N:9]([CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:8])[CH:21]=[O:22])#[N:12]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7237O-XyleneHCID 15416907HCID 15416907, compound

Product 1

HCID 21421756HCID 21421756, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred mixture of 110 parts of (-)-2-[N-(1-phenylethyl)amino]acetonitrile and 1500 parts of dimethylbenzene are added dropwise 70 parts of formic acid (slightly exothermic reaction). Upon completion, stirring is continued first for 3 hours at reflux temperature (water-separator) and further over week-end (about 63 hours) at room temperature. The reaction mixture is heated to 60° C and washed successively with water, a sodium bicarbonate solution, a diluted sodium hydroxide solution and again twice with water. The organic phase is separated, dried, filtered and evaporated. The residue is crystallized from a mixture of 80 parts of ethanol and 108 parts of 2,2'-oxybispropane. The product is filtered off and dried, yielding 46.5% of (-)-N-(cyanomethyl)-N-(1-phenylethyl)formamide; m.p. 78.8° C.; [α] = -60.7° (c = 1% CH3OH).

Workup

  1. customslightly exothermic reaction)
  2. waitfurther over week-end (about 63 hours) at room temperature
  3. washwashed successively with water
  4. customThe organic phase is separated
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is crystallized from a mixture of 80 parts of ethanol and 108 parts of 2,2'-oxybispropane
  9. filtrationThe product is filtered off
  10. customdried

Sources & evidence

ORD record
ord-2ba5420710ce4e57aaadd1f100dad806
Source dataset
uspto-grants-1976_11
Patent number
US03991072

Reaction notes

Loading…