Methanol → HCID 178448785, compound

HRID 1640036Notes

Reaction equation

HRID 1640036 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([SH:9])[S:8][C:4]=2[CH:3]=1.C(=O)CC[CH2:15][CH2:16][CH3:17].CO.[BH3-][C:22]#N.[Na+]>O.C(O)(=O)C>[CH3:22][CH:16]([CH3:15])[CH2:17][NH:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([SH:9])[S:8][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 6184HexanalHCID 5003444Sodium cyanoborohydrideHCID 178418618HCID 178418618, compound

Product 1

HCID 178448785HCID 178448785, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Into a 500 ml round bottomed flask were added 6-amino-1,3-benzothiazole-2-thiol (5.0 g, 0.03 mol), hexanal (3.0 g, 0.03 mol), methanol (250 ml), glacial acetic acid (2.5 ml), water (1 ml), and NaCNBH3 (1.9 g, 0.03 mol). The mixture was stirred for 4 h, filtered, and the filtrate was concentrated to give light yellow solid. The solid was washed with water and triturated with diethyl ether to give 4.0 g (61%) of the title compound. 1H NMR (DMSO-d5) δ=0.88 (t, 6H), 1.79 (m, 1H), 2.77 (t, 2H), 6.64 (d, 1H), 6.72 (s, 1H), 6.99 (d, 2H); ESIMS: m/z 239 (M−H).

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated
  3. customto give light yellow solid
  4. washThe solid was washed with water
  5. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-19d72c8ffef74a31a6fe0d24780483b6
Source dataset
uspto-grants-2012_02
Patent number
US08110686B2

Reaction notes

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