Thionyl Chloride → HCID 12790367, compound

HRID 1577633Notes

Reaction equation

HRID 1577633 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]2[O:11][C:12]([C:14]([OH:16])=O)=[CH:13][C:3]1=2.S(Cl)([Cl:19])=O>C1C=CC=CC=1>[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]2[O:11][C:12]([C:14]([Cl:19])=[O:16])=[CH:13][C:3]1=2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 13405807HCID 13405807, compound

Product 1

HCID 12790367HCID 12790367, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of sodium hydride (2.5 g) in dimethylformamide (100 ml), a solution of ethyl furo[3,2-b]indole-2-carboxylate (20 g) in dimethylformamide (100 ml) was added dropwise with stirring, then the mixture was stirred for 0.5 hour at room temperature. Methyl iodide (30 g) was added, and the resulting mixture was stirred for 5 hours at room temperature to give ethyl 4-methyl-furo[3,2-b]indole-2-carboxylate (18 g), which was hydrolyzed in a solution of sodium hydroxide (20 g) in water (200 ml) with stirring for an hour to give 4-methyl-furo[3,2-b]indole-2-carboxylic acid (15 g). This carboxylic acid was treated with thionyl chloride (50 ml) in benzene (70 ml) with stirring for an hour at 50° C. to give 4-methyl-furo[3,2-b]indole-2-carbonyl chloride (12 g).

Sources & evidence

ORD record
ord-c751c892f4484f028678b7e8a682a188
Source dataset
uspto-grants-1981_09
Patent number
US04288596

Reaction notes

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