Acetonitrile → 3-Ethyl-5-(3-methoxyethoxyethoxyethylnaphtho[2,1-d]thiazolin-2-ylidene)thiazolidine-4-on-2-thion

HRID 1449592Notes

Reaction equation

HRID 1449592 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][N:11]1[C:15]2[CH:16]=[CH:17][C:18]3[C:23]([C:14]=2[S:13][C:12]1=S)=[CH:22][CH:21]=[CH:20][CH:19]=3.C1(C)C=CC(S(OC)(=O)=O)=CC=1.[CH2:37]([N:39]1[C:43](=[O:44])[CH2:42][S:41][C:40]1=[S:45])[CH3:38].C(#N)C>C(N(CC)CC)C>[CH2:37]([N:39]1[C:43](=[O:44])[C:42](=[C:12]2[N:11]([CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[C:15]3[CH:16]=[CH:17][C:18]4[C:23]([C:14]=3[S:13]2)=[CH:22][CH:21]=[CH:20][CH:19]=4)[S:41][C:40]1=[S:45])[CH3:38]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6645Methyl p-toluenesulfonateHCID 820983-EthylrhodanineHCID 1317198163-Methoxyethoxyethoxyethylnaphtho[2,1-d]thiazoline-2-thion

Product 1

HCID 1317198173-Ethyl-5-(3-methoxyethoxyethoxyethylnaphtho[2,1-d]thiazolin-2-ylidene)thiazolidine-4-on-2-thion

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

1.9 g of 3-methoxyethoxyethoxyethylnaphtho[2,1-d]thiazoline-2-thion and 1.8 g of methyl p-toluenesulfonate were fed into a 50 ml short-neck flask provided with a reflux condenser. The resultant mixture was heated at 120° C. for 4 hours. After cooling the reaction mixture to room temperature followed by addition of 0.8 g of 3-ethylthiazolidine-4-on-2-thion and 24 ml of acetonitrile, the resultant mixture was cooled to 5° C., and 1.0 g of triethylamine was added thereto. After stirring at 10° C. for 24 hours, yellow precipitates thus obtained were suction-filtered, washed with 10 ml of acetonitrile three times, and dried to obtain the intended compound.

Workup

  1. customprovided with a reflux condenser
  2. customyellow precipitates thus
  3. customobtained
  4. filtrationwere suction-filtered
  5. washwashed with 10 ml of acetonitrile three times
  6. customdried
  7. customto obtain the intended compound

Sources & evidence

ORD record
ord-3f0d83a41a524566a50703d09940e657
Source dataset
uspto-grants-1997_02
Patent number
US05599825

Reaction notes

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