Chlorotrimethylsilane → HCID 131711643, compound

HRID 1659568Notes

Reaction equation

C(N(CC)CC)C.[CH3:8][C:9]1([CH3:21])[S:13][C@@H:12]2[C@H:14]([NH2:17])[C:15](=[O:16])[N:11]2[C@H:10]1[C:18]([OH:20])=[O:19].C[Si](C)(C)Cl.Cl[C:28]1[C:33]([O:34][C:35](=[O:52])[CH:36]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:37](OC2C=CC=CC=2)=[O:38])=[C:32](Cl)[C:31](Cl)=[C:30](Cl)[C:29]=1Cl.C(=O)(O)[O-].[Na+:61]>C(Cl)Cl>[Na+:61].[O:34]([C:35]([CH:36]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:37]([NH:17][CH:14]1[C:15](=[O:16])[N:11]2[CH:10]([C:18]([O-:20])=[O:19])[C:9]([CH3:21])([CH3:8])[S:13][C@H:12]12)=[O:38])=[O:52])[C:33]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 35 °C

Procedure

56 ml. (0.4 moles) of triethylamine are added to a suspension of 42 g. (0.2 moles) of 6-APA in 600 ml. of methylene chloride. Subsequently 430 g. (0.4 moles, 50 ml.) of trimethyl chlorosilane are added to the obtained solution at 10° C., and the mixture is stirred for 60 minutes. Thereafter the mixture is heated to 35° C., 104 g. (0.2 moles) of phenylmalonic acid phenylester pentachlorophenyl ester are added, and subsequently 28 ml. (0.2 moles) of triethylamine are introduced dropwise into the mixture. The reaction mixture is stirred at room temperature for 3 hours, thereafter it is neutralized to pH=7 with 200 ml. of 8% aqueous sodium bi-carbonate solution.

Workup

stirringThe reaction mixture is stirred at room temperature for 3 hours

Sources & evidence

ORD record: ord-c1613d8db6c441c092689aee94a291a4
Source dataset: uspto-grants-1981_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04304717

Reaction notes

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