Formic Acid → HCID 21421756, compound

HRID 259420Notes

Reaction equation

HRID 259420 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 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred mixture of 104.1 parts of (+)-2-[N-(1-phenylethyl)amino]acetonitrile and 1440 parts of dimethylbenzene are added dropwise 66 parts of formic acid (slightly exothermic reaction). Upon completion, stirring is continued for 3 hours at reflux temperature (water-separator). The reaction mixture is cooled to about 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 2,2'-oxybispropane. The product is filtered off, washed with 2,2'-oxybispropane and dried, yielding (+)-N-(cyanomethyl)-N-(1-phenylethyl)-formamide (41%); m.p. 78.9° C.; [α] = +60.90° (1% CH3OH).

Workup

  1. customslightly exothermic reaction)
  2. washwashed successively with water
  3. customThe organic phase is separated
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is crystallized from 2,2'-oxybispropane
  8. filtrationThe product is filtered off
  9. washwashed with 2,2'-oxybispropane
  10. customdried

Sources & evidence

ORD record
ord-54465646314644ed8e10e9b4cb336ba6
Source dataset
uspto-grants-1977_07
Patent number
US04038286

Reaction notes

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