2,6-Dichloroaniline → HCID 15725416, compound

HRID 358798Notes

Reaction equation

[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH2:4].[C:10]([C:12]1[C:13]([S:23](Cl)(=[O:25])=[O:24])=[N:14][N:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[N:17][C:16]=12)#[N:11]>N1C=CC=CC=1.CC(O)C>[C:10]([C:12]1[C:13]([S:23]([NH:4][C:3]2[C:2]([Cl:1])=[CH:8][CH:7]=[CH:6][C:5]=2[Cl:9])(=[O:24])=[O:25])=[N:14][N:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[N:17][C:16]=12)#[N:11]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 0.67 g (4.1 mmole) of 2,6-dichloroaniline was stirred at room temperature as a solution of 1.1 g (4.1 mmole) of 3-cyano-5,7-dimethylpyrazolo-[1,5-a]pyrimidine-2-sulfonyl chloride in 3 ml pyridine was added. The mixture was heated at 70° C. for 15 hours, then at 130° C. for 24 hours, and cooled to room temperature. The mixture was diluted with 2-propanol and stirred at room temperature for 1 hour. The tan solid was collected by filtration, washed well with 2-propanol and dried to give 0.9 g tan powder. This was completely dissolved in 2N NaOH and extracted with CH2Cl2. The aqueous layer was separated and acidified with glacial HOAc, which gave a precipitate. This was collected by filtration, washed well with water and dried to give 0.2 g (12.3 -percent) of the product as an off-white solid, m.p. 280°-285° C. (decomposition and degassing). 1H NMR (DMSO-d-6): 11.1 (br., 1H, NH), 7.5-7.4 (m, 3H, benzene), 7.5 (s, 1H, pyrazolopyrimidinyl H-6), 2.67 (s, 3H, CH3), 2.63 (s, 3H, CH3) 13C NMR (DMSO-d-6): 165, 156, 150, 148, 136, 130, 129, 114, 111, 80, 24, 16. IR (KBr): 3220, 2240, 1620, 1540, 1440, 1355, 1170 cm-1.

Workup

additionwas added
temperaturecooled to room temperature
filtrationThe tan solid was collected by filtration
washwashed well with 2-propanol
customdried

Sources & evidence

ORD record: ord-3afae0d0a8f3440591792ae2734c9220
Source dataset: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04997940

Reaction notes

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