Phosgene → 2H-Indazole, 3-chloro-2-(4-chloro-2-fluorophenyl)-4,5,6,7-tetrahydro-

HRID 2083123Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16](=O)[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[NH:9]2)=[C:4]([F:18])[CH:3]=1.C(Cl)([Cl:21])=O>ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([Cl:21])=[C:15]3[C:10]([CH2:11][CH2:12][CH2:13][CH2:14]3)=[N:9]2)=[C:4]([F:18])[CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Ten parts of 2-(4-chloro-2-fluorophenyl)-1,2,4,5,6,7-hexahydro-3H-indazol-3-one and 50 parts of chlorobenzene were charged to a Hastalloy C-lined shaker tube. The vessel was closed, charged with 10 parts of phosgene from a pressurized cylinder, and heated to 130° with constant shaking for 4 hours. The vessel was cooled to 25° C, vented, opened and discharged. The product mixture was evaporated under reduced pressure to give 10.1 parts of 2-(4-chloro-2-fluorophenyl)-3-chloro,4,5,6,7-tetrahydro-2H-indazole, m.p. 82°-85°. (90.7% pure as determined by gas chromatography).

Workup

customThe vessel was closed
temperatureheated to 130°
customThe product mixture was evaporated under reduced pressure

Sources & evidence

ORD record: ord-359ed1f213c6479b810bbaa326bd2452
Source dataset: uspto-grants-1978_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04084055

Reaction notes

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