Ethanethiol → HCID 135869713, compound

HRID 885013Notes

Reaction equation

HRID 885013 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[NH:6][C:7](=[O:27])[CH:8]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH3:26])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.CCS>C(Br)Br>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[NH:6][C:7](=[O:27])[CH:8]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH3:26])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6343EthanethiolHCID 59594405HCID 59594405, compound

Product 1

HCID 135869713HCID 135869713, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3024DibromomethaneSolvent

Procedure

To a solution of (Z)-7-chloro-5-(4-methoxyphenyl)-3-(2-methylbenzyl)-1H-benzo[e][1,4]diazepin-2(3H)-one precursor (0.6 g, 1.4 mmol) in CH2Br2 (20 mL) was added EtSH (7 mL) and then A1Br3 (1.7 g, 6.3 mmol, 4.5 eq). The resulting mixture was stirred overnight and then treated with ice (20 g) and after one hour filtered. The resulting solid was triturated with 50% DCM/heptane and then vacuum dried to give 445 mg (yield of 80%) of (Z)-7-chloro-5-(4-hydroxyphenyl)-3-(2-methylbenzyl)-1H-benzo[e][1,4]diazepin-2(3H)-one as a light yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 2.31 (s, 3H), 3.25-3.45 (m, 2H), 3.73 (dd, 1H), 6.80 (d, 2H), 7.02-7.18 (m, 3H), 7.2-7.3 (m, 5H), 7.64 (dd, 1H), 10.0 (br s, 1H), 10.7 (br s, 1H). MS, m/z 391.7 [M+1]

Workup

  1. filtrationfiltered
  2. customThe resulting solid was triturated with 50% DCM/heptane
  3. customvacuum dried

Sources & evidence

ORD record
ord-b648baa13d5b40248e3842f076b4f476
Source dataset
uspto-grants-2012_08
Patent number
US08242109B2

Reaction notes

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