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

HRID 1390218Notes

Reaction equation

HRID 1390218 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>CCOCC.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

Sulfo(2,3-dihydro-5-benzofuranyl)acetyl chloride is prepared according to the general procedure described in J. Med. Chem., 15, 1105 (1972). Sulfo(2,3-dihydro-5-benzofuranyl)acetic acid (20 mmole) is added slowly to a solution of ether (4 ml) and thionyl chloride (150 mmole). The mixture is stirred at room temperature until the gas evolution stopped. 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 ether and 30 ml of hexane and then cooled to -25° C. 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 -25° C
  3. customSulfo(2,3-dihydro-5-benzofuranyl)acetyl chloride is recovered from the mixture
  4. customused without further purification

Sources & evidence

ORD record
ord-6ece8161c25f42f381ae84e7369f6b79
Source dataset
uspto-grants-1979_02
Patent number
US04138397

Reaction notes

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