2,6-Difluorobenzoyl isocyanate → HCID 13262213, compound

HRID 2295797Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[C:18]2[O:17][C:16]([CH3:20])([CH3:19])[CH2:15][C:14]=2[CH:13]=[CH:12][CH:11]=1)[NH2:5].[F:21][C:22]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:23]=1[C:24]([N:26]=[C:27]=[O:28])=[O:25]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:27]([NH:26][C:24](=[O:25])[C:23]2[C:29]([F:33])=[CH:30][CH:31]=[CH:32][C:22]=2[F:21])=[O:28])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[C:18]2[O:17][C:16]([CH3:20])([CH3:19])[CH2:15][C:14]=2[CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Solution containing 4.0 g (13.8 m moles) of 3-chloro-4-(2,3-dihydro-2,2-dimethyl-7-benzofuranyloxy)aniline in 45 ml of toluene was placed under an atmosphere of nitrogen and heated to 70° C. To this was added 3.79 g (20 m moles) of 2,6-difluorobenzoyl isocyanate in 5 ml of toluene via an addition funnel. The resulting mixture was heated for 45 min. and then cooled to room temperature. The mixture was further cooled below 0° C. in a freezer and then filtered. The collected solid was washed with cold toluene. This was dried under vacuum to afford 5.43 g of the desired product as a white solid, mp 171° C. NMR (DMSO-d6): δ1.40 (s, 6H), 3.05 (s, 2H), 6.3-8.0 (m, 10H), 10.20 (broad s, 1H), 11.47 (broad s, 1H).

Workup

temperatureThe resulting mixture was heated for 45 min.
temperaturecooled to room temperature
temperatureThe mixture was further cooled below 0° C. in a freezer
filtrationfiltered
washThe collected solid was washed with cold toluene
customThis was dried under vacuum

Sources & evidence

ORD record: ord-b31bd89c449e49cfb6af780210d023d7
Source dataset: uspto-grants-1984_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04426385

Reaction notes

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