Thionyl Chloride → HCID 13476542, compound

Reaction equation

O[CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[NH:6][C:5]1=[O:15].S(Cl)([Cl:18])=O>>[Cl:18][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[NH:6][C:5]1=[O:15]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 13476541HCID 13476541, compound

Product 1

HCID 13476542HCID 13476542, compoundYield 86%

Procedure

A mixture of 3.6 parts of 1-(2-hydroxyethyl)-2,4(1H,3H)-quinazolinedione and 40 parts of thionyl chloride is stirred and refluxed overnight. The reaction mixture is allowed to cool to room temperature. The precipitated product is filtered off, washed with 2,2'-oxybispropane and dried, yielding 3.4 parts (86%) of 1-(2-chloroethyl)-2,4-(1H,3H)-quinazolinedione; mp. 215.3° C.

Workup

temperaturerefluxed overnight
filtrationThe precipitated product is filtered off
washwashed with 2,2'-oxybispropane
customdried

Sources & evidence

ORD record: ord-c5da8d98a7164fa885d9ed1288adb209
Source dataset: uspto-grants-1982_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04335127

Reaction notes

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