Water → HCID 13037004, compound

HRID 1855715Notes

Reaction equation

HRID 1855715 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]([NH2:10])[CH2:7][CH2:8][CH2:9][C:2]1=2.[C:11]1(=O)[O:16][C:14](=[O:15])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12.C(N(CC)CC)C.O>C1(C)C=CC=CC=1>[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]([N:10]3[C:14](=[O:15])[C:13]4=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]4[C:11]3=[O:16])[CH2:7][CH2:8][CH2:9][C:2]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 6811Phthalic AnhydrideHCID 8471TriethylamineHCID 42163724,5,6,7-Tetrahydro-1-benzothiophen-4-amine

Product 1

HCID 13037004HCID 13037004, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 50 ml of toluene, 5 g of 4,5,6,7-tetrahydrobenzo[b]thiophen-4-ylamine, 4.84 g of phthalic anhydride, and 0.5 ml of triethylamine are heated at reflux to azoetropically remove water. After the distillation of water is completed, the mixture is cooled, the crystals are collected and washed with ether to afford N-(4,5,6,7-tetrahydrobenzo[b]thien-4-yl)phthalimide, m.p. 166° C. to 167.5° C. Oxidation of this compound by the method of Example 1 affords the title compound, m.p. 163° C. to 166° C.

Workup

  1. distillationAfter the distillation of water
  2. temperaturethe mixture is cooled
  3. customthe crystals are collected
  4. washwashed with ether

Sources & evidence

ORD record
ord-5246fe08d7584002a16e60148e143616
Source dataset
uspto-grants-1980_08
Patent number
US04216149

Reaction notes

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