HCID 601594, compound → HCID 135581595, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]=[CH:10]OCC)=[CH:5][CH:4]=1.[Cl:14][C:15]1[C:16]2[CH:28]=[C:27]([OH:29])[CH:26]=[CH:25][C:17]=2[S:18][C:19]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21]>>[Cl:14][C:15]1[C:16]2[C:28]([CH:10]=[N:9][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)=[C:27]([OH:29])[CH:26]=[CH:25][C:17]=2[S:18][C:19]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21]Participants
3
Conditions
- Temperature
- 160 °C
Procedure
A round bottomed flask containing a mixture of the product from the previous reaction (6.04 g) and ethyl N-(4-methoxyphenyl)formimidate (4.50 g) was submerged rapidly in an oil bath pre-heated to 160° C., and the mixture stirred at 160-80° C. for 4 hours, the ethanol produced in the reaction being removed by distillation. More of the formimidate (0.80 g) was then added and the mixture heated at 180-90° C. for a further 1 hour. The cooled mixture was then treated with boiling methanol (100 ml) and the resulting light brown solid collected by filtration, washed with methanol (100 ml) and dried to give ethyl 3-chloro-5-hydroxy-4-[N-(4-methoxyphenyl)iminomethyl]benzo[b]thiophene-2-carboxylate (4.03 g); m.p. 162-163° C.
Workup
- additionA round bottomed flask containing
- additiona mixture of the product
- customwas submerged rapidly in an oil bath
- custombeing removed by distillation
- additionMore of the formimidate (0.80 g) was then added
- temperaturethe mixture heated at 180-90° C. for a further 1 hour
- additionThe cooled mixture was then treated with boiling methanol (100 ml)
- filtrationthe resulting light brown solid collected by filtration
- washwashed with methanol (100 ml)
- customdried
Sources & evidence
- ORD record
- ord-82c6b9800e204174bbf4d7b31cb32ef8
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353002B2
Reaction notes
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