1,2-Dichloro-3-isocyanatobenzene → 5-Tert-butyl-2-(3-(2,3-dichlorophenyl)ureido)thiophene-3-carboxylic acid

HRID 18919Notes

Reaction equation

[C:1]([C:5]1[S:9][C:8]([NH2:10])=[C:7]([C:11]([OH:13])=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1[N:22]=[C:23]=[O:24]>C1COCC1>[C:1]([C:5]1[S:9][C:8]([NH:10][C:23]([NH:22][C:16]2[CH:17]=[CH:18][CH:19]=[C:20]([Cl:21])[C:15]=2[Cl:14])=[O:24])=[C:7]([C:11]([OH:13])=[O:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 70 °C

Procedure

To a vial containing 5-tert-butyl-2-aminothiophene-3-carboxylic acid (1 mmol) in THF (7 mL) was added 2,3-dichlorophenyl isocyanate (1 mmol). The vial was capped and the solution was stirred at 70° C. for 21 hours. The reaction was cooled down to room temperature and the solvent was removed under vacuum. The oil residue was treated with dichloromethane and the resulting mixture was left to stand at room temperature for 1 hour. The solids were filtered, washed with minimal amount of dichloromethane and dried under vacuum to yield the expected 5-tert-butyl-2-(3-(2,3-dichlorophenyl)ureido)thiophene-3-carboxylic acid (317.2 mg, 83%). Coupling with the appropriate amine was performed as described above for Example 1.

Workup

customThe vial was capped
temperatureThe reaction was cooled down to room temperature
customthe solvent was removed under vacuum
additionThe oil residue was treated with dichloromethane
waitthe resulting mixture was left
waitto stand at room temperature for 1 hour
filtrationThe solids were filtered
washwashed with minimal amount of dichloromethane
customdried under vacuum

Sources & evidence

ORD record: ord-8027bc2a9abd4f80b73ba54cf7c729c5
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741479B2

Reaction notes

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