Acetic Anhydride → HCID 70575004, compound

HRID 1680490Notes

Reaction equation

HRID 1680490 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH2:20][C:21]2[NH:22][CH:23]=[CH:24][N:25]=2)=[CH:12]1>C(Cl)(Cl)Cl>[C:5]([NH:8][CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH2:20][C:21]2[NH:25][CH:24]=[CH:23][N:22]=2)=[CH:12]1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 70574771HCID 70574771, compound

Product 1

HCID 70575004HCID 70575004, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Acetic anhydride (0.20 g) was added dropwise to a stirred solution of 1-(2-aminoethyl)-3-(1-imidazolylmethyl)indole (0.48 g) in dry chloroform (10 ml) at room temperature. The solution was stirred for 10 minutes and then evaporated. The residue was stirred with aqueous sodium bicarbonate solution and the solid product was filtered off, washed with water, dried and crystallised from ethyl acetate/petrol (b.p. 60°-80° C.) to give 1-(2-acetylaminoethyl)-3-(1-imidazolylmethyl)indole (0.26 g), m.p. 126°-128° C. Found: C, 68.08; H, 6.43; N, 20.17. C16H18N4O requires: C, 68.06; H, 6.43; N, 19.85%.

Workup

  1. customevaporated
  2. stirringThe residue was stirred with aqueous sodium bicarbonate solution
  3. filtrationthe solid product was filtered off
  4. washwashed with water
  5. customdried
  6. customcrystallised from ethyl acetate/petrol (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-aaf94c233675499f9c2e133c0f4163aa
Source dataset
uspto-grants-1981_06
Patent number
US04273782

Reaction notes

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