2-Butanethione → 5-Chloro-2-methylindole

Reaction equation

Cl[NH:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][CH:4]=1.[CH3:10][CH2:11][C:12](=S)C>>[Cl:9][C:6]1[CH:5]=[C:4]2[C:3](=[CH:8][CH:7]=1)[NH:2][C:11]([CH3:12])=[CH:10]2

Participants

Reactant 2

HCID 95486922-Butanethione

HCID 12279953N,4-Dichloroaniline

Product 1

HCID 706365-Chloro-2-methylindoleYield 72%

Procedure

This compound was prepared from N-chloro-4-chloroaniline and methylthioacetone following Method A, which gave 6.68 g (0.032 mol, 72%) of the sub-titled product: mp. 64°-64.5° (recr. from cyclohexane ir (KBr) 3350 cm-1 (NH); pmr (CCl4), 2.42 (1H,s,NH), 2.52 and 3.15 (1 resp. 2H,m,aromatic H), 7.72 and 7.90 (3H, s, CH3 and SCH3).

Sources & evidence

ORD record: ord-590b9cfc97354c71818ff9f1474837bc
Source dataset: uspto-grants-1976_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03992392

Reaction notes

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