Dimethylformamide → Sulfo(2,3-dihydro-5-benzofuranyl)acetyl chloride

HRID 904021Notes

Reaction equation

HRID 904021 reaction equation
[S:1]([CH:5]([C:9]1[CH:10]=[CH:11][C:12]2[O:16][CH2:15][CH2:14][C:13]=2[CH:17]=1)[C:6](O)=[O:7])([OH:4])(=[O:3])=[O:2].S(Cl)([Cl:20])=O.CN(C)C=O>C(OCC)C.CCCCCC>[S:1]([CH:5]([C:9]1[CH:10]=[CH:11][C:12]2[O:16][CH2:15][CH2:14][C:13]=2[CH:17]=1)[C:6]([Cl:20])=[O:7])([OH:4])(=[O:3])=[O:2]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 23335828Sulfo(2,3-dihydro-5-benzofuranyl)acetic acid

Product 1

HCID 23335837Sulfo(2,3-dihydro-5-benzofuranyl)acetyl chloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

α-Sulfo(2,3-dihydro-5-benzofuranyl)acetyl chloride is prepared according to the general method described in J. Med. Chem., 15, 1105 (1972). α-Sulfo(2,3-dihydro-5-benzofuranyl)acetic acid 20 mmole is added slowly to a solution of diethyl ether (4 ml) and thionyl cloride (150 mmole). The mixture is stirred at room temperature until the gas evolution stops. Then about 0.2 ml of dimethylformamide is added and the solution heated at 40° C. for 4 hours. The mixture is diluted with 30 ml of diethyl ether and 30 ml of hexane and then cooled to about -25° C. The α-sulfo(2,3-dihydro-5-benzofuranyl)acetyl chloride is recovered from the mixture and used without further purification.

Workup

  1. temperaturethe solution heated at 40° C. for 4 hours
  2. temperaturecooled to about -25° C
  3. customThe α-sulfo(2,3-dihydro-5-benzofuranyl)acetyl chloride is recovered from the mixture
  4. customused without further purification

Sources & evidence

ORD record
ord-0e28808bc4294e2ebc41f61c37ed1708
Source dataset
uspto-grants-1980_10
Patent number
US04229575

Reaction notes

Loading…