Chloroacetonitrile → HCID 15733239, compound

HRID 2397573Notes

Reaction equation

HRID 2397573 reaction equation
[H-].[Na+].[C:3]1([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([Cl:18])[CH:16]=3)[NH:11][C:10]=2[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[CH2:25][C:26]#[N:27]>CN(C)C=O>[C:26]([CH2:25][N:11]1[C:12]2[C:17](=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[C:10]1[C:19]([O:21][CH2:22][CH3:23])=[O:20])#[N:27]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 737953ethyl 5-chloro-3-phenyl-1H-indole-2-carboxylate

Product 1

HCID 15733239HCID 15733239, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (from 7.2 gms., 0.15 mole 50% sodium hydride dispersed in mineral oil) in 125 ml fresh dimethyl formamide (DMF) is added ethyl 3-phenyl-5-chloroindole-2-carboxylate (45 gms, 0.15 mole), as a dry powder, in portions. The reaction is exothermic and requires a water bath to maintain the temperature between 45°-50° C. After stirring 15-20 minutes (at 35° C), chloroacetonitrile (12 grams, 0.15 mole) in 25 ml DMF is added slowly. The temperature rises to 45° C and the mixture is stirred overnight at ambient temperature. The mixture is then transferred to a one liter beaker and 500 ml of ice-water is added slowly. After 15-20 minutes the product is filtered off, washed well with water, and dried on a Buchner funnel. After recrystallization from ethanol the product gives a m.p. of 117°-19° C. There is obtained a total of 46 grams (90.2%), of sufficient purity for the next step. A sample is recrystallized from aqueous ethanol, washed with water and vacuum dried, m.p. 119°-120° C.

Workup

  1. temperatureto maintain the temperature between 45°-50° C
  2. additionis added slowly
  3. customrises to 45° C
  4. additionis added slowly
  5. filtrationAfter 15-20 minutes the product is filtered off
  6. washwashed well with water
  7. customdried on a Buchner funnel
  8. customAfter recrystallization from ethanol the product
  9. customgives a m.p. of 117°-19° C
  10. customThere is obtained a total of 46 grams (90.2%)
  11. customA sample is recrystallized from aqueous ethanol
  12. washwashed with water and vacuum
  13. customdried

Sources & evidence

ORD record
ord-ac4d55390852422c846518622bc24d20
Source dataset
uspto-grants-1977_05
Patent number
US04022778

Reaction notes

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