Diethylcarbamoyl chloride → HCID 54127150, compound

HRID 1957433Notes

Reaction equation

[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[CH:5]=1)([CH3:3])[CH3:2].BrN1C(=O)CCC1=O.C([Li])CCC.[CH2:27]([N:29]([CH2:33][CH3:34])[C:30](Cl)=[O:31])[CH3:28]>>[CH:1]([C:4]1[CH:5]=[C:6]([O:12][CH3:13])[C:7]([O:10][CH3:11])=[CH:8][C:9]=1[C:30]([N:29]([CH2:33][CH3:34])[CH2:27][CH3:28])=[O:31])([CH3:3])[CH3:2]

Participants

Reactant 4

HCID 6916Diethylcarbamoyl chloride

HCID 67184N-bromobutanimide

HCID 10910154HCID 10910154, compound

HCID 178418339Butyllithium

Product 1

HCID 54127150HCID 54127150, compound

Procedure

Thirty-one grams of 4-isopropyl-1,2-dimethoxybenzene was treated with N-bromosuccinimide followed by butyllithium and diethyl carbamyl chloride as in preparation 6B to yield 15.2 g of 2-isopropyl-4,5-dimethoxy-N,N-diethylbenzamide as a viscous oil. The benzamide was treated according to preparation 18B with butyllithium and sulfur dioxide followed by sulfuryl chloride then ammonia to provide 4.5 g of the sulfonamide, mp 181°-182° C. from ether. This was cyclized in acetic acid as in preparation 18B to obtain 2.86 g of 6,7-dimethoxy-4-isopropylsaccharin, mp 210°-212° C. from ethyl acetate-hexane.

Sources & evidence

ORD record: ord-af28d62032e2403484d8d706e35b3463
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05783589

Reaction notes

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