Dimethyl oxalate → HCID 178499141, compound

HRID 2051711Notes

Reaction equation

HRID 2051711 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]([NH2:26])(C(C(C1C=CC=CC=1)C1C=CC=CC=1)=O)[C:5](=O)[C:6]([O:8][CH3:9])=[O:7].COC(=O)C(C([CH:35]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=O)N.COC(=O)C(OC)=O.C[O-].[Na+].[S-:60][C:61]#[N:62].[K+]>>[CH:35]([N:62]1[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:3]([O:2][CH3:1])=[O:27])[N:26]=[C:61]1[SH:60])([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

6

Reactant 5

HCID 11120Dimethyl oxalateHCID 516872Potassium thiocyanateHCID 10942334Sodium MethoxideHCID 56997143HCID 56997143, compoundHCID 57071968HCID 57071968, compound

Product 1

HCID 178499141HCID 178499141, compound

Procedure

In the manner described in Example (1a) 36.9 g (0.01 mol) of 2-(benzhydrylformyl)-amino-3-oxo-succinic acid dimethyl ester (prepared by reacting (benzhydrylformyl)-aminoacetic acid methyl ester with oxalic acid dimethyl ester in the presence of sodium methylate) were reacted with 18 g of potassium thiocyanate for 48 hours at 50° C. The 1-benzhydryl-2-mercapto-4,5-dimethoxycarbonyl-imidazole formed crystallized on adding hexane. Yield 33.2 g (87% of the theory), m.p. 154° C.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-19fb1ce44dc5472282627480daadb6cc
Source dataset
uspto-grants-1980_01
Patent number
US04182624

Reaction notes

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