Water → HCID 22180711, compound

HRID 484753Notes

Reaction equation

HRID 484753 reaction equation
[NH2:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]#[N:12])=[CH:8][C:7]([S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:6][CH:5]=2.[H-].[Na+].[C:22](=O)([O:26]C1C=CC=CC=1)[O:23][CH2:24][CH3:25].O>CN(C)C=O.C(O)(=O)C>[C:11]([C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:8]=2)[NH:3][C:2]=1[NH:1][C:22](=[O:26])[O:23][CH2:24][CH3:25])#[N:12]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 138067Carbonic acid, ethyl phenyl esterHCID 146332Amphethinile

Product 1

HCID 22180711HCID 22180711, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled solution of 2-amino-3-cyano-5-(phenylthio)indole (1.5 g., 5.7mM.) in dimethyl formamide (20 ml.) was added sodium hydride (0.27 g., 50% w/w dispersion in mineral oil, 5.7mM.) followed by ethyl phenyl carbonate (0.94 g., 5.7mM.). The mixture was stirred overnight and allowed to warm to room temperature. T.l.c. indicated the reaction was complete. The reaction mixture was poured into rapidly stirred water and neutralised with acetic acid. The cream-coloured precipitate was filtered off and dried to give the crude product (1.62 g.) m.p. 181°-2° C. Recrystallisation from ethanol gave colourless crystals of ethyl 3-cyano-5-(phenylthio)indol-2-ylcarbamate, m.p. 190.5°-191.5° C. (0.82 g., 43%). ##STR2##

Workup

  1. filtrationThe cream-coloured precipitate was filtered off
  2. customdried
  3. customto give the crude product (1.62 g.) m.p. 181°-2° C
  4. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-d039b00107074bd7925deb5b053a3fdc
Source dataset
uspto-grants-1985_08
Patent number
US04533672

Reaction notes

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