Dimethyl Sulfate → HCID 15170289, compound

HRID 1165670Notes

Reaction equation

S(OC)(O[CH3:5])(=O)=O.[CH:8]1[C:16]2[C:15]3[S:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[C:14]=3[CH:13]=[CH:12][C:11]=2[NH:10][C:9]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25]>>[CH3:5][N:10]1[C:11]2[CH:12]=[CH:13][C:14]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[S:17][C:15]=3[C:16]=2[CH:8]=[C:9]1[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

Reactant 2

HCID 6497Dimethyl Sulfate

HCID 15170288HCID 15170288, compound

Product 1

HCID 15170289HCID 15170289, compound

Procedure

Using the procedure outlined in Example 34A except that dimethyl sulfate was used as the alkylating agent, ethyl 3H-[1]benzothieno[2,3-e]indole-2-carboxylate (H. G. Pars Pharmaceutical Laboratories, Inc.) gave a nearly quantitative yield of crude ethyl 3-methyl-3H-[1]benzothieno[2,3-e]indole-2-carboxylate. This material was formylated using the procedure of A. Rieche et al., Chem. Ber. 93, 88 (1960) to give a crude mixture of aldehydes which was hydrolyzed and decarboxylated without purification using the procedure outlined in Example 15B to give a 19.0% yield of 3-methyl-3H-[1]benzothieno[2,3-e]indole-1-carbaldehyde·0.25 H2O, mp 223.5°-224°, (CH2Cl2 /hexane), (C,H,N).

Sources & evidence

ORD record: ord-63a76aa0734e4fdaaa48345a446fdfbc
Source dataset: uspto-grants-1990_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04910218

Reaction notes

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