Thioglycolic Acid → HCID 178479822, compound

HRID 1427322Notes

Reaction equation

HRID 1427322 reaction equation
[ClH:1].Cl.[N:3]1[NH:4][N:5]=[N:6][C:7]=1[C:8]1[CH:9]=[C:10]([NH2:15])[C:11]([NH2:14])=[CH:12][CH:13]=1.[SH:16][CH2:17][C:18](O)=O>Cl>[ClH:1].[N:6]1[NH:5][N:4]=[N:3][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]2[NH:14][C:18]([CH2:17][SH:16])=[N:15][C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 1133Thioglycolic Acid2×HCID 67299086HCID 67299086, compound

Product 1

HCID 178479822HCID 178479822, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
110 °C

Procedure

To 4-(2H-tetrazol-5-yl)-benzene-1,2-diamine dihydrochloride (9.40 g, 37.7 mmol) in 50% (v/v) hydrochloric acid (105 ml). 2-mercaptoacetic acid (2.4 ml, 3.18 g, 34.5 mmol) was added and the reaction mixture heated under nitrogen at 110° C. for 48 hours. Additional mercaptoacetic acid (0.5 ml, 0.66 g, 7.20 mmol) was added after 24 hours. The reaction mixture was cooled and a sample analysed by hplc. The greenish coloured solid was filtered off and washed with water. The solid was dried at 50° C. under a vacuum (90 mBar) to yield [5-(2H-tetrazol-5-yl)-1H-benzoimidazol-2-yl]-methanethiol hydrochloride (5.27 g, 65% yield), Rt=7.4 mins, purity by HPLC>97%. 1H NMR (d6-DMSO, 400 MHz) 8.49 ppm (1H, m), 8.22 ppm (1H, dd, 8.8 Hz, 1.6 Hz), 7.95 ppm (1H, m, 9.2 Hz), 4.67 ppm (0.3H, s), 4.24 ppm (2H, s). MS: (Electrospray+) 233.0 m/z (M+H), 463.0 m/z (2M−H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationThe greenish coloured solid was filtered off
  3. washwashed with water
  4. customThe solid was dried at 50° C. under a vacuum (90 mBar)

Sources & evidence

ORD record
ord-ce242090d3cc4c3bb726d1526ed4d218
Source dataset
uspto-grants-2015_01
Patent number
US08933206B2

Reaction notes

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