Dimethylthiocarbamoyl chloride → HCID 178447889, compound

HRID 435095Notes

Reaction equation

HRID 435095 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:15]=[CH:14][C:13](S)=[C:12]([Br:17])[CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[CH2:18]([C@H:21]1[CH2:26][CH2:25][C@H:24]([C:27]2[CH:32]=[CH:31][C:30](O)=[C:29]([Br:34])[CH:28]=2)[CH2:23][CH2:22]1)[CH2:19][CH3:20].CN(C)[C:37](Cl)=[S:38].[CH2:41]([O:43][C:44]1[CH:51]=[CH:50][C:47]([CH2:48]Br)=[CH:46][CH:45]=1)[CH3:42]>>[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:48]([S:38][CH:37]([C:30]3[CH:31]=[CH:32][C:27]([C@H:24]4[CH2:25][CH2:26][C@H:21]([CH2:18][CH2:19][CH3:20])[CH2:22][CH2:23]4)=[CH:28][C:29]=3[Br:34])[C:47]3[CH:50]=[CH:51][C:44]([O:43][CH2:41][CH3:42])=[CH:45][CH:46]=3)[C:47]3[CH:50]=[CH:51][C:44]([O:43][CH2:41][CH3:42])=[CH:45][CH:46]=3)=[C:12]([Br:17])[CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

5

Reactant 4

HCID 27871Dimethylthiocarbamoyl chlorideHCID 147756681-(Bromomethyl)-4-ethoxybenzeneHCID 178447900HCID 178447900, compoundHCID 178447920HCID 178447920, compound

Product 1

HCID 178447889HCID 178447889, compound

Procedure

31.5 g of 4-(trans-4-n-propylcyclohexyl)-2-bromothiophenol [prepared from 4-(trans-4-n-propylcyclohexyl)-2-bromophenol obtained according to Example 3 by reaction with dimethylthiocarbamoyl chloride, thermal rearrangement and hydrolysis analogously to Organic Syntheses, Volume 51 (1971), pages 139-142] is etherified with 21.5 g of 4-ethoxybenzyl bromide analogously to Example 1(d). There is obtained 40.2 g of 4-(trans-4-n-propylcyclohexyl)-2-bromophenyl-(4-ethoxybenzyl)thioether.

Workup

  1. customobtained
  2. customthermal rearrangement and hydrolysis analogously to Organic Syntheses, Volume 51 (1971), pages 139-142]

Sources & evidence

ORD record
ord-9f05703a65b54b159173f8d5fa1535b0
Source dataset
uspto-grants-1983_08
Patent number
US04400293

Reaction notes

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