Triethylamine → HCID 86736898, compound

HRID 1395635Notes

Reaction equation

[NH2:1][C:2]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:3]=1[NH:4][S:5]([CH3:8])(=[O:7])=[O:6].C(N(CC)CC)C.[F:23][S:24]([C:27]1[CH:28]=C(S(Cl)(=O)=O)[CH:30]=[CH:31][CH:32]=1)(=[O:26])=[O:25]>O1CCCC1>[NH2:1][C:2]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:3]=1[N:4]([NH:4][S:5]([CH3:8])(=[O:7])=[O:6])[S:5]([C:8]1[CH:30]=[CH:31][CH:32]=[C:27]([S:24]([F:23])(=[O:25])=[O:26])[CH:28]=1)(=[O:7])=[O:6]

Participants

Conditions

Temperature: 5 °C

Procedure

2'-Amino-4'-nitromethanesulfonanilide (30.4 g; 0.13 mole) was dissolved in dry tetrahydrofuran (ca. 700 ml) and then triethylamine (13.1 g; 0.13 mole) was added and the solution was chilled to 5° C. While stirring and maintaining a temperature <10° C., While stirring and maintaining a temperature <10° C., m-fluorosulfonylbenzenesulfonyl chloride (33.8 g; 0.13 mole) was added dropwise. After the addition, the reaction was kept at the ice bath temperature for one hour and then stirring continued at room temperature for an additional hour. The reaction solution was poured into ice cold water (about 2 liters) while stirring and scratching vigorously. The product was filtered and dried to yield 50.6 g (85 percent) beige solid, m.p. 204° to 209° C. A small sample (1 g) was recrystallized from ethanol (150 ml) to yield a beige solid, m.p. 224° to 226° C.

Workup

temperaturemaintaining a temperature <10° C.
stirringWhile stirring
additionwas added dropwise
additionAfter the addition
stirringstirring
waitcontinued at room temperature for an additional hour
stirringwhile stirring
filtrationThe product was filtered
customdried

Sources & evidence

ORD record: ord-dd262aabefff404ba0fb38bed0af86c7
Source dataset: uspto-grants-1980_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04204993

Reaction notes

Loading…