Water → 4-[4-(2,5-Dichlorobenzoyl)phenoxy]benzene-1-sulfonyl chloride

HRID 1374045Notes

Reaction equation

P(Cl)(Cl)([Cl:3])=O.CN(C)C(=O)C.O.[Cl:13][C:14]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:15]=1[C:16]([C:18]1[CH:34]=[CH:33][C:21]([O:22][C:23]2[CH:28]=[CH:27][C:26]([S:29](O)(=[O:31])=[O:30])=[CH:25][CH:24]=2)=[CH:20][CH:19]=1)=[O:17]>C(#N)C.S1(CCCC1)(=O)=O>[Cl:13][C:14]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:15]=1[C:16]([C:18]1[CH:34]=[CH:33][C:21]([O:22][C:23]2[CH:28]=[CH:27][C:26]([S:29]([Cl:3])(=[O:31])=[O:30])=[CH:25][CH:24]=2)=[CH:20][CH:19]=1)=[O:17]

Participants

Conditions

Temperature: 72 °C

Procedure

To 215 g (about 400 mmol) of the crude crystal of A-SO3Na, 300 mL of acetonitrile and 200 mL of sulfolane as a solvent were added, and further phosphoryl trichloride (245.3 g, 1.6 mole) was added and then reacted at 70° C. to obtain a reaction mixture. Further, 5 mL of N,N-dimethyl acetoamide was added thereto and the resulting yellow suspension was stirred at 71 to 73° C. for 40 min and then cooled to 3° C. To the suspension, 1 L of cool water was added at a rate such that the temperature of the reaction system was not over 10° C. The resulting precipitate was collected, washed with cool water and re-crystallized with 350 mL of toluene to obtain 153 g of the aimed white crystalline A-SO2Cl having a melting point of from 130.5 to 131.5° C. (yield: 87% on the basis of A). The IR spectrum is shown in FIG. 4 and the NMR spectrum is shown in FIGS. 5 and 6.

Workup

customreacted at 70° C.
customto obtain a reaction mixture
temperaturecooled to 3° C
customwas not over 10° C
customThe resulting precipitate was collected
washwashed with cool water
customre-crystallized with 350 mL of toluene

Sources & evidence

ORD record: ord-54bb713ec685444fb35ec4e85ddd523b
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07163988B2

Reaction notes

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