Sulfuryl chloride → Pyrrolo(3,4-e)-1,4-diazepin-2(1H)-one, 3,7-dihydro-8-chloro-6,7-dimethyl-5-phenyl-

HRID 1074415Notes

Reaction equation

S(Cl)([Cl:4])(=O)=O.[CH3:6][C:7]1[N:8]([CH3:24])[CH:9]=[C:10]2[C:16]=1[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[N:14][CH2:13][C:12](=[O:23])[NH:11]2.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:4][C:9]1[N:8]([CH3:24])[C:7]([CH3:6])=[C:16]2[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:14][CH2:13][C:12](=[O:23])[NH:11][C:10]=12

Participants

Conditions

Temperature: -60 °C

Procedure

A solution of freshly distilled sulphuryl chloride (4.0 ml) in methylene chloride (40 ml) is added dropwise over a period of 20 minutes to a solution of 3,7-dihydro-6,7-dimethyl-5-phenylpyrrolo[3,4-e][1,4]diazepin-2(1H)-one (5.0 g) in methylene chloride (80 ml) cooled to -60° C. and maintained under inert atmosphere. The reaction is allowed to proceed at -55° C.±5° C. for one hour, then the reaction mixture is poured into a 5% aqueous solution of NaHCO3 (210 ml) and vigorously stirred for 20 minutes. The organic phase is separated, washed with water, dried and evaporated to dryness under vacuum. The obtained residue is crystallized from ethanol yielding 3.7 g of the compound of the title. M.p. 195° C. with decomposition.

Workup

temperaturemaintained under inert atmosphere
customThe organic phase is separated
washwashed with water
customdried
customevaporated to dryness under vacuum
customThe obtained residue is crystallized from ethanol yielding 3.7 g of the compound of the title

Sources & evidence

ORD record: ord-8e679ee2a4954c7a8ab23763ed9b0bdc
Source dataset: uspto-grants-1983_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04391817

Reaction notes

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