Dimethylamine → 2-[(Dimethylamino)sulfonylmethyl]benzoic acid

Liquified dimethylamine (73 ml) was added slowly with cooling to a 15% (w/w) solution of methyl 2-[(chlorosulfonyl)methyl]benzoate (42.0 g) in chlorobenzene. When addition was complete, the suspension was stirred 0.5 hour at room temperature, then filtered. The filtrate was concentrated to approximately 250 ml and added dropwise to a mixture of 150 ml of ethanol, 50 ml of water and 40 ml of 50% sodium hydroxide. The resulting suspension was stirred overnight at room temperature. The reaction solution was concentrated to dryness and the residue partitioned between 1000 ml water and 1000 ml of methylene chloride for 1.5 hour. The aqueous phase was separated, washed with 400 ml of methylene chloride, then acidified with concentrated hydrochloric acid. The precipitated solid was collected and dried overnight in vacuo to give 34.9 of 2-[(dimethylamino)sulfonylmethyl]benzoic acid, m.p. 112°-119°.

1. additionWhen addition
2. filtrationfiltered
3. concentrationThe filtrate was concentrated to approximately 250 ml
4. additionadded dropwise to a mixture of 150 ml of ethanol, 50 ml of water and 40 ml of 50% sodium hydroxide
5. stirringThe resulting suspension was stirred overnight at room temperature
6. concentrationThe reaction solution was concentrated to dryness
7. customthe residue partitioned between 1000 ml water and 1000 ml of methylene chloride for 1.5 hour
8. customThe aqueous phase was separated
9. washwashed with 400 ml of methylene chloride
10. customThe precipitated solid was collected
11. customdried overnight in vacuo

ORD record

ord-50b8393122a84f64bcbdad8b9ee4ac12

Source dataset

uspto-grants-1987_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04678500