Acetic Acid → HCID 19977088, compound

HRID 2399715Notes

Reaction equation

HRID 2399715 reaction equation
NCC[C:4]1[S:8][C:7]2[CH:9]=[CH:10][C:11]([C:13]3[N:14]=[N:15][N:16]([CH3:18])[N:17]=3)=[CH:12][C:6]=2[CH:5]=1.[C:19]([BH3-])#[N:20].[Na+].[C:23](O)(=O)[CH3:24].C=O.[C:29](=O)([O-])[O-].[K+].[K+]>CO>[CH3:29][N:20]([CH2:23][CH2:24][C:5]1[C:6]2[CH:12]=[C:11]([C:13]3[N:14]=[N:15][N:16]([CH3:18])[N:17]=3)[CH:10]=[CH:9][C:7]=2[S:8][CH:4]=1)[CH3:19]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 67691731HCID 67691731, compound

Product 1

HCID 19977088HCID 19977088, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a mixture of -(2-aminoethyl)-5-(2-methyltetrazol-5-yl)benzo[b]thiophene (0.372 g, 1.43 mmol) and sodium cyanoborohydride (0.136 g, 2.15 mmol) in methanol (3 ml) and acetic acid (0.247 ml, 4.30 mmol) cooled in an ice bath was added 38% w/v formaldehyde solution (0.453 ml, 5.74 mmol) in methanol (3 ml) dropwise over 5 min and the mixture was stirred at room temperature for 3 h. After this time, saturated potassium carbonate solution (30 ml) was added and the mixture was extracted with ethyl acetate (3×50 ml). The combined extracts were evaporated in vacuo to leave 0.53 g. Chromatography on flash silica, eluting with 10-30% methanol/dichloromethane, gave 0.335 g (81%) of the title product as a colourless oil. The oxalate salt was prepared using oxalic add in methanol/ether to give the title product oxalate as a white solid, m.p. 214°-218° C. Analysis found: C, 50.58; H, 4.80; N, 18.28%. Calcd for C14H17N5S. C2H2O: C, 50.92; H, 5.07; N, 18.56%. δ (DMSO) 2.84 (6H, s), 3.30-3.42 (4H, m), 4.46 (3H, s), 7.69 (1H, s), 8.06 (1H, dd, J=8.4 and 1.4 Hz), 8.20 (1H, d, J= 8.4 Hz), 8.56 (1H, s). m/z (CI+,NH3) 288 (M+H)+.

Workup

  1. temperaturecooled in an ice bath
  2. additionwas added 38%
  3. customdropwise over 5 min
  4. extractionthe mixture was extracted with ethyl acetate (3×50 ml)
  5. customThe combined extracts were evaporated in vacuo
  6. customto leave 0.53 g
  7. washChromatography on flash silica, eluting with 10-30% methanol/dichloromethane

Sources & evidence

ORD record
ord-093d1861bfd244488174cc71b6f5e838
Source dataset
uspto-grants-1995_09
Patent number
US05451588

Reaction notes

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