Chloroacetonitrile → HCID 54556287, compound

HRID 1728321Notes

Reaction equation

HRID 1728321 reaction equation
[C:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]=[C:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH2:27][C:28]#[N:29]>CN(C=O)C>[O:22]=[C:20]1[N:19]([CH2:27][C:28]#[N:29])[C:18](=[O:23])[C:17](=[CH:16][C:13]2[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:11][CH:12]=2)[S:21]1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 5213866HCID 5213866, compound

Product 1

HCID 54556287HCID 54556287, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-[4-(2-phenylethoxy)phenylmethylene]-2,4-thiazolidinedione Example 4 (1.0 g, 3.07 mmol) in 25 ml dry DMF was treated with NaH (0.1 g, 4.2 mmol) and stirred at room temperature for 10 min. The mixture was treated with chloroacetonitrile (0.3 g, 4 mmol) and stirred at room temperature for 24 h. The mixture was poured into 500 ml ice water, and the resulting tan solid was collected by filtration, washed with water, and dried to give the desired product in 75% (1.0 g) yield; mp 155-157° C.; NMR(CDCl3TMS): δ3.13 (t, 2H, ArCH2), 4.25 (t, 2H, OCH2), 4.60 (s, 2H, CH2CN), [7.00 (d, 2H), 7.45 (d, 2H) OPh], 7.26 (m, 5H, Ph), 7.94 (s, 1H, C=CH); Anal calcd for C20H16N2O2S, MW 364.42: C, 65.92; H, 4.43; N, 7.69; S, 8.80. Found: C, 66.15; H, 4.24; N, 7.93; S, 8.69. Mass spec m/e 365(M+1).

Workup

  1. stirringstirred at room temperature for 24 h
  2. filtrationthe resulting tan solid was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-7ace5ab1bcaa4da49b7d73596201b61c
Source dataset
uspto-grants-1994_07
Patent number
US05326770

Reaction notes

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