Acetic Acid → N-(7-Oxo-4,5,6,7-tetrahydro-1-benzothiophen-4-yl)formamide

HRID 2163446Notes

Reaction equation

HRID 2163446 reaction equation
[CH:1]([NH:3][CH:4]1[C:12]2[CH:11]=[CH:10][S:9][C:8]=2[CH2:7][CH2:6][CH2:5]1)=[O:2].[Cl-].[Na+].C(O)(=[O:17])C>>[CH:1]([NH:3][CH:4]1[C:12]2[CH:11]=[CH:10][S:9][C:8]=2[C:7](=[O:17])[CH2:6][CH2:5]1)=[O:2]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 5234Sodium ChlorideHCID 93944Formamide, N-(4,5,6,7-tetrahydrobenzo[b]thien-4-yl)-

Product 1

HCID 23347790N-(7-Oxo-4,5,6,7-tetrahydro-1-benzothiophen-4-yl)formamide

Procedure

In 725 ml of 50% aqueous acetic acid, 39 g of N-formyl-4,5,6,7-tetrahydrobenzo[b]thiophen-4-amine is stirred while 473 g of ceric ammonium nitrate is added over 15 minutes at about 25° C. After 15 minutes of additional stirring, sodium chloride is added and the mixture is extracted 3 times with dichloromethane (500, 500 and 250 ml). The combined extract is washed with brine and then with water. The water is extracted with 100 ml of dichloromethane and combined with the main dichloromethane solution. Evaporation of the dichloromethane in vacuo gives a sticky gum, which when triturated with 100 ml of ether affords 28.4 g. of the title compound, m.p. 96° C. to 106° C.

Workup

  1. additionis added over 15 minutes at about 25° C
  2. extractionthe mixture is extracted 3 times with dichloromethane (500, 500 and 250 ml)
  3. extractionThe combined extract
  4. washis washed with brine
  5. extractionThe water is extracted with 100 ml of dichloromethane
  6. customEvaporation of the dichloromethane in vacuo
  7. customgives a sticky gum, which when
  8. customtriturated with 100 ml of ether
  9. customaffords 28.4 g

Sources & evidence

ORD record
ord-0d8e0892b51c4ccea1459ed7142ef5c3
Source dataset
uspto-grants-1979_01
Patent number
US04134899

Reaction notes

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